Refrigerant compositions containing a compatibilizer

ABSTRACT

The present invention provides compositions that are useful for compatabilizing a conventional, non-polar, compression refrigeration lubricant and a hydrofluorocarbon and/or hydrochlorofluorocarbon refrigerant in a compression refrigeration apparatus. Additionally, these composition promote efficeint return of lubricant from the non-compressor zones to the compressor zones of the aforesaid refrigeration apparatus.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the priority benefit of U.S. ProvisionalApplication 60/254,208, filed Dec. 8, 2000, and U.S. ProvisionalApplication 60/304,552, filed Jul. 11, 2001.

FIELD OF THE INVENTION

The present invention relates to refrigerant compositions comprisingrelatively polar, halogenated hydrocarbon refrigerant; relativelynon-polar, conventional, compression refrigeration lubricant; and acompound that compatibilizes said polar halogenated hydrocarbon andnon-polar lubricant. The compatibilizer decreases the viscosity of thelubricant in the coldest portions of a compression refrigerationapparatus by solubilizing halogenated hydrocarbon and lubricant, whichresults in efficient return of the lubricant from non-compressor zonesto a compressor zone in a compression refrigeration system.

BACKGROUND

Over the course of the last twenty (20) years it has been debatedwhether the release of chlofluorocarbons into the atmosphere haseffected the stratospheric ozone layer. As a result of this debate andinternational treaties, the refrigeration and air-conditioningindustries have been weaning themselves from the use and production ofcertain chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs).Presently, the industries are transitioning towards the use ofhydrofluorocarbons (HFCs) having zero ozone depletion potential.Notably, this transition to HFCs necessitated the advent of a new classof lubricants because of the immiscibility of conventional lubricants,such as mineral oil, poly α-olefin and alkylbenzene with HFCrefrigerants.

The new class of lubricants includes polyalkylene glycols (PAGs) andpolyol esters (POEs) lubricants. While the PAG and POE lubricants havesuitable lubricant properties, they are extremely hygroscopic and canabsorb several thousand ppm (parts per million) of water on exposure tomoist air. This absorbed water leads to undesirable formation of acidsthat cause corrosion of the refrigeration system and formation ofintractable sludges. In comparison, conventional refrigerationlubricants are considerably less hygroscopic and have low solubility,less than 100 ppm for water. Further, PAGs and POEs are considerablymore expensive than conventional refrigeration lubricants—typically onthe order of three to six times more. PAGs and POEs have also been foundto have unfavorable electrical insulating properties.

Accordingly, there existed a need and an opportunity to resolve thissolubility problem so that the refrigeration industry could utilize theconventional non-polar mineral oil and alkylbenzene lubricants withpolar HFC-based refrigerants. Another need and opportunity also existedwhen the industry began transitioning towards the use of HCFC-basedrefrigerants as a replacement for pure CFC refrigerants. This needbecame apparent due to the diminished solubility of HCFCs in mineraloil, which forced the industry to incurr an additional expense ofchanging the lubricant to an alkylbenzene to achieve adequatelubricating and cooling performance.

For the last ten years the refrigeration and air-conditioning industrieshave been struggling with these long-felt but unsolved needs, finally,the present invention satisfies the pressing needs of these industries.While numerous attempts have been made to use conventional non-polarlubricants with polar hydrofluorocarbon refrigerants, the lack ofsolubility of the polar refrigerant in the non-polar conventionallubricant generally results in a highly viscous lubricant in thenon-compressor zones, which unfortunately results in insufficientlubricant return to the compressor. When the non-polar conventionallubricant and the polar refrigerant naturally escape the compressor andenter the non-compressor zones, phase separation/insolubilty of thelubricant and the refrigerant occurs. This phase separation contributesto the highly viscous lubricant remaining in the non-compressor zone,whilst the refrigerant continues its path throughout the refrigerationsystem. The insolubility and highly viscous nature of the lubricantleaves the lubricant stranded in the non-compressor zones, which leadsto an undesirable accumulation of lubricant in the non-compressor zones.This accumulation of lubricant and the lack of return of the lubricantto the compressor zone eventually starves the compressor of lubricantand results in the compressor overheating and seizing. Such strandedlubricant may also decrease the efficiency of the refrigeration systemby interfering with heat transfer, due to thick lubricant filmsdeposited on interior surfaces of the heat exchangers (e.g. condensorand evaporator). Further, during cold compressor starts, insolublerefrigerant and lubricant may cause compressor seizure due to poorlubrication and foaming of the lubricant.

For the foregoing reasons, there is a well-recognized need in therefrigeration and air-conditioning industries for a compatabilizer thatcompatibilizes a polar halogenated hydrocarbon and a non-polarconventional lubricant in a compression refrigeration system, andpromotes efficient return of lubricant to the compressor.

SUMMARY

The present invention is directed to lubricant and refrigerantcompositions containing a compatibilizer that satisfies therefrigeration and air-conditioning industries's problem of insolubilitybetween conventional non-polar compression refrigeration lubricants andpolar hydrofluorocarbon and/or hydrochlorofluorocarbon refrigerants. Thecompatibilizers decrease the viscosity of the non-polar lubricant in thecoldest portions of a compression refrigeration apparatus bysolubilizing the polar halogenated hydrocarbon and lubricant in thenon-compressor zones, which results in efficient return of lubricantfrom non-compressor zones to a compressor zone. The present invention isalso directed to processes for returning lubricant from a non-compressorzone to a compressor zone in a compression refrigeration system, methodsof solubilizing a halogenated hydrocarbon refrigerant in a lubricant, aswell as methods of lubricating a compressor in a compressionrefrigeration apparatus containing a halogenated hydrocarbonrefrigerant.

The present invention comprises lubricant compositions for use incompression refrigeration and air conditioning apparatus comprising: (a)at least one lubricant selected from the group consisting of paraffins,napthenes, aromatics and poly-α-olefins, and (b) at least onecompatibilizer. The present invention further comprises refrigerantcompositions for use in compression refrigeration and air conditioningcomprising: (a) at least one halogenated hydrocarbon selected from thegroup consisting of hydrofluorocarbons and hydrochlorofluorocarbons; (b)at least one lubricant selected from the group consisting of paraffins,napthenes, aromatics and poly-α-olefins; and (c) at least onecompatibilizer. The present invention further comprises compositions foruse in compression refrigeration and air conditioning apparatuscontaining paraffinic, napthenic, aromatic and/or poly-α-olefiniclubricant comprising: (a) at least one halogenated hydrocarbon selectedfrom the group consisting of hydrofluorocarbons andhydrochlorofluorocarbons; and (b) at least one compatibilizer.

The present invention also provides processes for returning lubricantfrom a non-compressor zone to a compressor zone in a compressionrefrigeration system comprising: (a) contacting a lubricant selectedfrom the group consisting of paraffins, naphthenes, aromatics, andpolyalphaolefins, in said non-compressor zone with a halogenatedhydrocarbon selected from the group consisting of hydrofluorocarbons andhydrochlorofluorocarbons, in the presence of a compatibilizer to form asolution comprising said lubricant, said halogenated hydrocarbon, andsaid compatibilizer; and (b) transferring said solution from saidnon-compressor zone to said compressor zone of said refrigerationsystem.

The present invention further provides methods of solubilizing ahalogenated hydrocarbon refrigerant selected from the group consistingof hydrofluorocarbons and hydrochlorofluorocarbons, in a lubricantselected from the group consisting of paraffins, naphthenes, aromatics,and polyalphaolefins, which comprise the steps of contacting saidlubricant with said halogenated hydrocarbon refrigerant in the presenceof an effective amount of a compatibilizer and forming a solution ofsaid lubricant and said halogenated hydrocarbon refrigerant.

The present invention further pertains to methods of lubricating acompressor in a compression refrigeration apparatus containing ahalogenated hydrocarbon refrigerant selected from the group consistingof hydrofluorocarbons and hydrochlorofluorocarbons, comprising the stepof adding to said compressor a composition comprising: (a) at least onelubricant selected from the group consisting of paraffins, naphthenes,aromatics, and polyalphaolefins; and (b) at least one compatibilizer.The present invention also pertains to a method for delivering acompatibilizer to a compression refrigeration apparatus.

The lubricants and/or refrigerant compositions, as well as the abovedescribed methods and/or processes can optionally include a fragrance.

Compatibilizers of the present invention include:

(i) polyoxyalkylene glycol ethers represented by the formulaR¹[(OR²)_(x)OR³]_(y), wherein: x is selected from integers from 1 to 3;y is selected from integers from 1 to 4; R¹ is selected from hydrogenand aliphatic hydrocarbon radicals having 1 to 6 carbon atoms and ybonding sites; R² is selected from aliphatic hydrocarbylene radicalshaving from 2 to 4 carbon atoms; R³ is selected from hydrogen, andaliphatic and alicyclic hydrocarbon radicals having from 1 to 6 carbonatoms; at least one of R¹ and R³ is selected from said hydrocarbonradicals; and wherein said polyoxyalkylene glycol ethers have amolecular weight of from about 100 to about 300 atomic mass units and acarbon to oxygen ratio of from about 2.3 to about 5.0;

(ii) amides represented by the formulae R¹CONR²R³ andcyclo-[R⁴CON(R⁵)—], wherein R¹, R², R³ and R⁵ are independently selectedfrom aliphatic and alicyclic hydrocarbon radicals having from 1 to 12carbon atoms; R⁴ is selected from aliphatic hydrocarbylene radicalshaving from 3 to 12 carbon atoms; and wherein said amides have amolecular weight of from about 120 to about 300 atomic mass units and acarbon to oxygen ratio of from about 7 to about 20,

(iii) ketones represented by the formula R¹COR², wherein R¹ and R² areindependently selected from aliphatic, alicyclic and aryl hydrocarbonradicals having from 1 to 12 carbon atoms, and wherein said ketones havea molecular weight of from about 70 to about 300 atomic mass units and acarbon to oxygen ratio of from about 4 to about 13,

(iv) nitrites represented by the formula R¹CN, wherein R¹ is selectedfrom aliphatic, alicyclic or aryl hydrocarbon radicals having from 5 to12 carbon atoms, and wherein said nitrites have a molecular weight offrom about 90 to about 200 atomic mass units and a carbon to nitrogenratio of from about 6 to about 12,

(v) chlorocarbons represented by the formula RCl_(x), wherein; x isselected from the integers 1 or 2; R is selected from aliphatic andalicyclic hydrocarbon radicals having from 1 to 12 carbon atoms; andwherein said chlorocarbons have a molecular weight of from about 100 toabout 200 atomic mass units and carbon to chlorine ratio from about 2 toabout 10,

(vi) aryl ethers represented by the formula R¹OR², wherein: R¹ isselected from aryl hydrocarbon radicals having from 6 to 12 carbonatoms; R² is selected from aliphatic hydrocarbon radicals having from 1to 4 carbon atoms; and wherein said aryl ethers have a molecular weightof from about 100 to about 150 atomic mass units and a carbon to oxygenratio of from about 4 to about 20,

(vii) 1,1,1-trifluoroalkanes represented by the formula CF₃R¹, whereinR¹ is selected from aliphatic and alicyclic hydrocarbon radicals havingfrom about 5 to about 15 carbon atoms; and

(viii) fluoroethers represented by the formula R¹OCF₂CF₂H, wherein R¹ isselected from aliphatic and alicyclic hydrocarbon radicals having fromabout 5 to about 15 carbon atoms.

In the compositions of the present invention, the weight ratio of saidlubricant to said compatibilizer is from about 99:1 to about 1:1.

BRIEF DESCRIPTION OF THE FIGURES

The present invention is better understood with reference to thefollowing figures, where:

FIG. 1 is a graph of phase separation temperature (“PST”)(° C.) versuscarbon to oxygen ratio for various polyoxyalkylene glycol ethercompatibilizers (25 wt %), HFC-134a refrigerant (50 wt %) and Zerol® 150(alkyl benzene lubricant from Shrieve Chemicals) (25 wt %).

FIG. 2 is a graph of phase separation temperature (° C.) versus carbonto oxygen ratio for various polyoxyalkylene glycol ether compatibilizers(10 wt %), R401A refrigerant (50 wt %) and Suniso® 3GS (mineral oillubricant from Crompton Co.) (40 wt %).

FIG. 3 is a graph of phase separation temperature (° C.) versus carbonto oxygen ratio for various ketone compatibilizers (25 wt %), HFC-134arefrigerant (50 wt %) and Zerol® 150 (25 wt %).

FIG. 4 is a graph of phase separation temperature (° C.) versus carbonto nitrogen ratio for various nitrile compatibilizers (25 wt %),HFC-134a refrigerant (50 wt %) and Zerol® 150 (25 wt %).

FIG. 5 is a graph of phase separation temperature (° C.) versus carbonto chlorine ratio for various chlorocarbon compatibilizers (25 wt %),HFC-134a refrigerant (50 wt %) and Zerol® 150 (25 wt %).

FIG. 6 is a graph of phase separation temperature (° C.) versus carbonto chlorine ratio for various chlorocarbon compatibilizers (10 wt %),R401A refrigerant (50 wt %) and Suniso® 3GS (40 wt %).

FIG. 7 is a graph of phase separation temperature (° C.) versus carbonto oxygen ratio for various amide compatibilizers (25 wt %), HFC-134arefrigerant (50 wt %) and Zero® 150 (25 wt %).

FIG. 8 is a graph of phase separation temperature (° C.) versus carbonto oxygen ratio for various amide compatibilizers (10 wt %), R401Arefrigerant (50 wt %) and Suniso® 3GS (40 wt %).

FIG. 9 shows graphs of phase separation temperature (° C.) versus carbonto oxygen ratio for various polyoxyalkylene glycol ether compatibilizers(25 wt %), Zerol® 150 (25 wt %) and refrigerant HFC-32, HFC-125 or R410A(50 wt %).

FIG. 10 is a graph of dynamic viscosity versus temperature for POE22(Mobil Oil product Arctic EAL22, a polyol ester lubricant having akinematic viscosity of 22 cs at 40° C.), Zerol® 150 and the composition:10 wt % Propylene glycol n-butyl ether (PnB), 5 wt % Dipropylene glycoln-butyl ether (DPnB) and 85 wt % Zerol® 150.

These and other features, aspects, and advantages of the presentinvention will become better understood with reference to the followingdescription and the appended claims.

DETAILED DESCRIPTION

The present inventors discovered that using an effective amount of thepresent compatibilizers in conventional compression refrigerationlubricants results in efficient return of lubricant from non-compressorzones to a compressor zone in a compression refrigeration system. Thecompatibilizers travel throughout a compression refrigeration systemmixed with refrigerant and with lubricant that escapes the compressor.Use of compatibilizers results in the decrease of the viscosity oflubricant in the coldest portions of compression refrigeration systems,such as an evaporator, thereby enabling return of the lubricant from theevaporator to the compressor. The inventors discovered that theviscosity of lubricant in the coldest sections of compressionrefrigeration systems is reduced upon use of the presentcompatibilizers. This reduction in lubricant viscosity is due to anincrease in solubility of halogenated hydrocarbon refrigerants inlubricant containing the compatibilizers. Through control of the ratioof carbon to polar groups (e.g. ether, carbonyl, nitrile, halogen) inthe compatibilizer, the inventors discovered that the polargroup-containing compatibilizer could surprisingly be caused to remainmiscible with the essentially non-polar lubricants in the coldestsections of compression refrigeration apparatus and simultaneouslyincrease the solubility of halogenated hydrocarbon refrigerant in thelubricant. Without wishing to be bound by theory, the polar functionalgroups in the present compatibilizers are attracted to the relativelypolar halogenated hydrocarbon refrigerant while the hydrocarbon portionof the compatibilizer is miscible with the relatively low polaritylubricant. The result upon use of the present compatibilizers in thepresent conventional lubricants is an increase in the solubility ofhalogenated hydrocarbon refrigerants in lubricant containing aneffective amount of compatibilizer. This increased solubility of therelatively nonviscous halogenated hydrocarbon refrigerant inconventional lubricants leads to lowering of the viscosity of thelubricant, and results in efficient return of lubricant fromnon-compressor zones to a compressor zone in a compression refrigerationsystem. Reducing the amount of lubricant in the evaporator zone alsoimproves heat transfer of the refrigerant and thus improvesrefrigerating capacity and efficiency of a system. Thus, the presentcompatibilizers allow for the use of relatively polar halogenatedhydrocarbon refrigerants, such as hydrofluorocarbons andhydrochlorofluorocarbons, with relatively non-polar conventionallubricants; mixtures which are normally immiscible and previouslythought to be not useful together as refrigerant compositions incompression refrigeration systems.

The result of increased solubility of halogenated hydrocarbonrefrigerants in conventional lubricants further allows liquidrefrigerant to dissolve and carry stranded lubricant out of thecondenser, improving both lubricant return and heat transfer in thecondenser and resulting in improved capacity and efficiency of therefrigeration system.

The present compatibilizers improve the energy efficiency and capacityof a compression refrigeration system by increasing the enthalpy changeupon desorption of halogenated hydrocarbon refrigerant from lubricantand compatibilizer composition in the evaporator, as well as absorptionof refrigerant into the lubricant and compatibilizer composition in thecondenser. Without wishing to be bound by theory, it is believed thatforming and breaking attractions between the refrigerant and the polarfunctional group-containing compatibilizer results in the increase inenthalpy change.

In most instances, the volume resistivity (ohmxcm) of polyol ester andpolyalkylene glycol lubricants presently used withhydrofluorocarbon-based refrigerants is unacceptably low. The presentcompositions comprising compatibilizer and conventional lubricant haveincreased volume resistivity versus polyol ester and polyalkylene glycollubricants.

The present compatibilizers may benefically increase the viscosity indexof conventional lubricants. This gives the desirable result of lowerviscosity at low temperature without significantly lowering viscosity athigh temperature, a viscosity profile similar to that of many polyolesters. Such a viscosity index ensures lubricant return from theevaporator while maintaining acceptable viscosity for compressoroperation.

In the present compositions comprising lubricant and compatibilizer,from about 1 to about 50 weight percent, preferably from about 6 toabout 45 weight percent, and most preferably from about 10 to about 40weight percent of the combined lubricant and compatibilizer compositionis compatibilizer. In terms of weight ratios, in the presentcompositions comprising lubricant and compatibilizer, the weight ratioof lubricant to compatibilizer is from about 99:1 to about 1:1,preferably from about 15.7:1 to about 1.2:1, and most preferably fromabout 9:1 to about 1.5:1. Compatibilizer may be charged to a compressionrefrigeration system as a composition of compatibilizer and halogenatedhydrocarbon refrigerant. When charging a compression refrigerationsystem with the present compatibilizer and halogenated hydrocarbonrefrigerant compositions, to deliver an amount of compatibilizer suchthat the aforementioned relative amounts of compatibilizer and lubricantare satisfied, the compatibilizer and halogenated hydrocarbonrefrigerant composition will typically contain from about 0.1 to about40 weight percent, preferably from about 0.2 to about 20 weight percent,and most preferably from about 0.3 to about 10 weight percentcompatibilizer in the combined compatibilizer and halogenatedhydrocarbon refrigerant composition. In compression refrigerationsystems containing the present compositions comprising halogenatedhydrocarbon refrigerant, lubricant and compatibilizer, from about 1 toabout 70 weight percent, preferably from about 10 to about 60 weightpercent of the halogenated hydrocarbon refrigerant, lubricant andcompatibilizer composition is lubricant and compatibilizer.Compatibilizer concentrations greater than about 50 weight percent ofthe combined lubricant and compatibilizer composition are typically notneeded to obtain acceptable lubricant return from non-compressor zonesto a compressor zone. Compatibilizer concentrations greater than about50 weight percent of the combined lubricant and compatibilizercomposition can negatively influence the viscosity of the lubricant,which can lead to inadequate lubrication and stress on, or mechanicalfailure of, the compressor. Further, compatibilizer concentrationshigher than about 50 weight percent of the combined lubricant andcompatibilizer composition can negatively influence the refrigerationcapacity and performance of a refrigerant composition in a compressionrefrigeration system. An effective amount of compatibilizer in thepresent compositions leads to halogenated hydrocarbon and lubricantbecoming solubilized to the extent that adequate return of lubricant ina compression refrigeration system from non-compressor zones (e.g.evaporator or condenser) to the compressor zone is obtained.

Halogenated hydrocarbon refrigerants of the present invention contain atleast one carbon atom and one fluorine atom. Of particular utility arehalogenated hydrocarbons having 1-6 carbon atoms containing at least onefluorine atom, optionally containing chlorine and oxygen atoms, andhaving a normal boiling point of from −90° C. to 80° C. Thesehalogenated hydrocarbons may be represented by the general formulaC_(w)F_(2w+2−x−y)H_(x)Cl_(y)O_(z), wherein w is 1-6, x is 1-9, y is 0-3,and z is 0-2. Preferred of the halogenated hydrocarbons are those inwhich w is 1-6, x is 1-5, y is 0-1, and z is 0-1. The present inventionis particularly useful with hydrofluorocarbon andhydrochlorofluorocarbon-based refrigerants. Halogenated hydrocarbonrefrigerants are commercial products available from a number of sourcessuch as E. I. du Pont de Nemours & Co., Fluoroproducts, Wilmington,Del., 19898, USA, or are available from custom chemical synthesiscompanies such as PCR Inc., P.O. Box 1466, Gainesville, Fla., 32602,USA, and additionally by synthetic processes disclosed in art such asThe Journal of Fluorine Chemistry, or Chemistry of Organic FluorineCompounds, edited by Milos Hudlicky, published by The MacMillan Company,New York, N.Y., 1962. Representative halogenated hydrocarbons include:CHClF₂ (HCFC-22), CHF₃ (HFC-23), CH₂F₂ (HFC-32), CH₃F (HFC-41), CF₃CF₃(FC-116), CHClFCF₃ (HCFC-124), CHF₂CF₃ (HFC-125), CH₂ClCF₃ (HCFC-133a),CHF₂CHF₂ (HFC-134), CH₂FCF₃ (HFC-134a), CClF₂CH₃ (HCFC-142b), CHF₂CH₂F(HFC-143), CF₃CH₃ (HFC-143a), CHF₂CH₃ (HFC-152a), CHF₂CF₂CF₃(HFC-227ca), CF₃CFHCF₃ (HFC-227ea), (HFC-236ca), CH₂FCF₂CF₃ (HFC-236cb),CHF₂CHFCF₃ (HFC-236ea), CF₃CH₂CF₃ (HFC-236fa), CH₂FCF₂CHF₂ (HFC-245ca),CH₃CF₂CF₃ (HFC-245cb), CHF₂CHFCHF₂ (HFC-245ea), CH₂FCHFCF₃ (HFC-245eb),CHF₂CH₂CF₃ (HFC-245fa), CH₂FCF₂CH₂F (HFC-254ca), CH₂CF₂CHF₂ (HFC-254cb),CH₂FCHFCHF₂ (HFC-254ea), CH₃CHFCF₃ (HFC-254eb), CHF₂CH₂CHF₂ (HFC-254fa),CH₂FCH₂CF₃ (HFC-254fb), CH₃CF₂CH₃ (HFC-272ca), CH₃CHFCH₂F (HFC-272ea),CH₂FCH₂CH₂F (HFC-272fa), CH₃CH₂CF₂H (HFC-272fb), CH₃CHFCH₃ (HFC-281ea),CH₃CH₂CH₂F (HFC-281fa), CHF₂CF₂CF₂CF₂H (HFC-338pcc), CF₃CHFCHFCF₂CF₃(HFC-43-10mee), C₄F₉OCH₃, and C₄F₉OC₂H₅.

The present invention is particularly useful with the hydrofluorocarbonand hydrochlorofluorocarbon-based refrigerants, such as, CHClF₂(HCFC-22), CHF₃ (HFC-23), CH₂F₂ (HFC-32), CHClFCF₃ (HCFC-124), CHF₂CF₃(HFC-125), CHF₂CHF₂ (HFC-134), CH₂FCF₃ (HFC-134a), CF₃CH₃ (HFC-143a),CHF₂CH₃ (HFC-152a), CHF₂CF₂CF₃ (HFC-227ca), CF₃CFHCF₃ (HFC-227ea),CF₃CH₂CF₃ (HFC-236fa), CHF₂CH₂CF₃ (HFC-245fa), CHF₂CF₂CF₂CF₂H(HFC-338pcc), CF₃CHFCHFCF₂CF₃ (HFC-43-10mee); and the azeotropic andazeotrope-like halogenated hydrocarbon refrigerant compositions, suchas, HCFC-22/HFC-152a/HCFC-124 (known by the ASHRAE designations, R-401A,R-401B, and R-401C), HFC-125/HFC-143a/HFC-134a (known by the ASHRAEdesignation, R-404A), HFC-32/HFC-125/HFC-134a (known by ASHRAEdesignations, R-407A, R-407B, and R-407C), HCFC-22/HFC-143a/HFC-125(known by the ASHRAE designation, R-408A), HCFC-22/HCFC-124/HCFC-142b(known by the ASHRAE designation: R-409A), HFC-32/HFC-125 (R-410A), andHFC-125/HFC-143a (known by the ASHRAE designation: R-507).

The halogenated hydrocarbons of the present invention may optionallyfurther comprise up to 10 weight percent of dimethyl ether, or at leastone C₃ to C₅ hydrocarbon, e.g., propane, propylene, cyclopropane,n-butane, i-butane, and n-pentane. Examples of halogenated hydrocarbonscontaining such C₃ to C₅ hydrocarbons are azeotrope-like compositions ofHCFC-22/HFC-125/propane (known by the ASHRAE designation, R-402A andR-402B) and HCFC-22/octafluoropropane/propane (known by the ASHRAEdesignation, R-403A and R-403B).

Lubricants of the present invention are those conventionally used incompression refrigeration apparatus utilizing chlorofluorocarbonrefrigerants. Such lubricants and their properties are discussed in the1990 ASHRAE Handbook, Refrigeration Systems and Applications, chapter 8,titled “Lubricants in Refrigeration Systems”, pages 8.1 through 8.21,herein incorporated by reference. Lubricants of the present inventionare selected by considering a given compressor's requirements and theenvironment to which the lubricant will be exposed. Lubricants of thepresent invention preferrably have a kinematic viscosity of at leastabout 15 cs (centistokes) at 40° C. Lubricants of the present inventioncomprise those commonly known as “mineral oils” in the field ofcompression refrigeration lubrication. Mineral oils comprise paraffins(i.e. straight-chain and branched-carbon-chain, saturated hydrocarbons),naphthenes (i.e. cyclic paraffins) and aromatics (i.e. unsaturated,cyclic hydrocarbons containing one or more rings characterized byalternating double bonds). Lubricants of the present invention furthercomprise those commonly known as “synthetic oils” in the field ofcompression refrigeration lubrication. Synthetic oils comprisealkylaryls (i.e. linear and branched alkyl alkylbenzenes), syntheticparaffins and napthenes, and poly(alphaolefins). Representativeconventional lubricants of the present invention are the commerciallyavailable BVM 100 N (paraffinic mineral oil sold by BVA Oils), Suniso®3GS (napthenic mineral oil sold by Crompton Co.), Sontex® 372LT(napthenic mineral oil sold by Pennzoil), Calumet® RO-30 (napthenicmineral oil sold by Calument Lubricants), Zerol® 75 and Zerol® 150(linear alkylbenzenes sold by Shrieve Chemicals) and HAB 22 (branchedalkylbenzene sold by Nippon Oil).

Compatibilizers of the present invention comprise polyoxyalkylene glycolethers represented by the formula R¹[(OR²)_(x)OR³]_(y), wherein: x isselected from integers from 1-3; y is selected from integers from 1-4;R¹ is selected from hydrogen and aliphatic hydrocarbon radicals having 1to 6 carbon atoms and y bonding sites; R² is selected from aliphatichydrocarbylene radicals having from 2 to 4 carbon atoms; R³ is selectedfrom hydrogen and aliphatic and alicyclic hydrocarbon radicals havingfrom 1 to 6 carbon atoms; at least one of R¹ and R³ is said hydrocarbonradical; and wherein said polyoxyalkylene glycol ethers have a molecularweight of from about 100 to about 300 atomic mass units and a carbon tooxygen ratio of from about 2.3 to about 5.0. In the presentpolyoxyalkylene glycol ether compatibilizers represented byR¹[(OR²)_(x)OR³]_(y): x is preferably 1-2; y is preferably 1; R¹ and R³are preferably independently selected from hydrogen and aliphatichydrocarbon radicals having 1 to 4 carbon atoms; R² is preferablyselected from aliphatic hydrocarbylene radicals having from 2 or 3carbon atoms, most preferably 3 carbon atoms; the polyoxyalkylene glycolether molecular weight is preferably from about 100 to about 250 atomicmass units, most preferably from about 125 to about 250 atomic massunits; and the polyoxyalkylene glycol ether carbon to oxygen ratio ispreferably from about 2.5 to 4.0 when hydrofluorocarbons are used ashalogenated hydrocarbon refrigerant, most preferably from about 2.7 toabout 3.5 when hydrofluorocarbons are used as halogenated hydrocarbonrefrigerant, and preferably from about 3.5 to 5.0 whenhydrochlorofluorocarbon-containing refrigerants are used as halogenatedhydrocarbon refrigerant, most preferably from about 4.0 to about 4.5when hydrochlorofluorocarbon-containing refrigerants are used ashalogenated hydrocarbon refrigerant. The R¹ and R³ hydrocarbon radicalshaving 1 to 6 carbon atoms may be linear, branched or cyclic.Representative R¹ and R³ hydrocarbon radicals include methyl, ethyl,propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,isopentyl, neopentyl, tert-pentyl, cyclopentyl, and cyclohexyl. Wherefree hydroxyl radicals on the present polyoxyalkylene glycol ethercompatibilizers may be incompatible with certain compressionrefrigeration apparatus materials of construction (e.g. Mylaru®), R¹ andR³ are preferably aliphatic hydrocarbon radicals having 1 to 4 carbonatoms, most preferably 1 carbon atom. The R² aliphatic hydrocarbyleneradicals having from 2 to 4 carbon atoms form repeating oxyalkyleneradicals —(OR²)_(x)— that include oxyethylene radicals, oxypropyleneradicals, and oxybutylene radicals. The oxyalkylene radical comprisingR² in one polyoxyalkylene glycol ether compatibilizer molecule may bethe same, or one molecule may contain different R² oxyalkylene groups.The present polyoxyalkylene glycol ether compatibilizers preferablycomprise at least one oxypropylene radical. Where R¹ is an aliphatic oralicyclic hydrocarbon radical having 1 to 6 carbon atoms and y bondingsites, the radical may be linear, branched or cyclic. Representative R¹aliphatic hydrocarbon radicals having two bonding sites include, forexample, an ethylene radical, a propylene radical, a butylene radical, apentylene radical, a hexylene radical, a cyclopentylene radical and acyclohexylene radical. Representative R¹ aliphatic hydrocarbon radicalshaving three or four bonding sites include residues derived frompolyalcohols, such as trimethylolpropane, glycerin, pentaerythritol,1,2,3-trihydroxycyclohexane and 1,3,5-trihydroxycyclohexane, by removingtheir hydroxyl radicals. Representative polyoxyalkylene glycol ethercompatibilizers include: CH₃OCH₂CH(CH₃)O(H or CH₃) (propylene glycolmethyl (or dimethyl) ether), CH₃O[CH₂CH(CH₃)O]₂(H or CH₃) (dipropyleneglycol methyl (or dimethyl) ether), CH₃O[CH₂CH(CH₃)O]₃(H or CH₃)(tripropylene glycol methyl (or dimethyl) ether), C₂H₅OCH₂CH(CH₃)O(H orC₂H₅) (propylene glycol ethyl (or diethyl) ether), C₂H₅O[CH₂CH(CH₃)O]₂(Hor C₂H₅) (dipropylene glycol ethyl (or diethyl) ether),C₂H₅O[CH₂CH(CH₃)O]₃(H or C₂H₅) (tripropylene glycol ethyl (or diethyl)ether), C₃H₇OCH₂CH(CH₃)O(H or C₃H₇) (propylene glycol n-propyl (ordi-n-propyl) ether), C₃H₇O[CH₂CH(CH₃)O]₂(H or C₃H₇) (dipropylene glycoln-propyl (or di-n-propyl) ether), C₃H₇O[CH₂CH(CH₃)O]₃(H or C₃H₇)(tripropylene glycol n-propyl (or di-n-propyl) ether), C₄H₉OCH₂CH(CH₃)OH(propylene glycol n-butyl ether), C₄H₉O[CH₂CH(CH₃)O]₂(H or C₄H₉)(dipropylene glycol n-butyl (or di-n-butyl) ether),C₄H₉O[CH₂CH(CH₃)O]₃(H or C₄H₉) (tripropylene glycol n-butyl (ordi-n-butyl) ether), (CH₃)₃COCH₂CH(CH₃)OH (propylene glycol t-butylether), (CH₃)₃CO[CH₂CH(CH₃)O]₂(H or (CH₃)₃) (dipropylene glycol t-butyl(or di-t-butyl) ether), (CH₃)₃CO[CH₂CH(CH₃)O]₃(H or (CH₃)₃)(tripropylene glycol t-butyl (or di-t-butyl) ether), C₅H₁₁OCH₂CH(CH₃)OH(propylene glycol n-pentyl ether), C₄H₉OCH₂CH(C₂H₅)OH (butylene glycoln-butyl ether), C₄H₉O[CH₂CH(C₂H₅)O]₂H (dibutylene glycol n-butyl ether),trimethylolpropane tri-n-butyl ether (C₂H₅C(CH₂O(CH₂)₃CH₃)₃) andtrimethylolpropane di-n-butyl ether (C₂H₅C(CH₂OC(CH₂)₃CH₃)₂CH₂OH).

Compatibilizers of the present invention further comprise amidesrepresented by the formulae R¹CONR²R³ and cyclo-[R⁴CON(R⁵)—], whereinR¹, R², R³ and R⁵ are independently selected from aliphatic andalicyclic hydrocarbon radicals having from 1 to 12 carbon atoms; R⁴ isselected from aliphatic hydrocarbylene radicals having from 3 to 12carbon atoms; and wherein said amides have a molecular weight of fromabout 120 to about 300 atomic mass units and a carbon to oxygen ratio offrom about 7 to about 20. The molecular weight of said amides ispreferably from about 160 to about 250 atomic mass units. The carbon tooxygen ratio in said amides is preferably from about 7 to about 16, andmost preferably from about 10 to about 14. R¹, R², R³ and R⁵ mayoptionally include substituted hydrocarbon radicals, that is, radicalscontaining non-hydrocarbon substituents selected from halogens (e.g.,fluorine, chlorine) and alkoxides (e.g. methoxy). R¹, R², R³ and R⁵ mayoptionally include heteroatom-substituted hydrocarbon radicals, that is,radicals which contain the atoms nitrogen (aza-), oxygen (oxa-) orsulfur (thia-) in a radical chain otherwise composed of carbon atoms. Ingeneral, no more than three non-hydrocarbon substituents andheteroatoms, and preferably no more than one, will be present for each10 carbon atoms in R¹⁻³, and the presence of any such non-hydrocarbonsubstituents and heteroatoms must be considered in applying theaforementioned ratio of carbon to oxygen and molecular weightlimitations. Preferred amide compatibilizers consist of carbon,hydrogen, nitrogen and oxygen. Representative R¹, R², R³ and R⁵aliphatic and alicyclic hydrocarbon radicals include methyl, ethyl,propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl,octyl, nonyl, decyl, undecyl, dodecyl and their configurational isomers.A preferred embodiment of amide compatibilizers are those wherein R⁴ inthe aforementioned formula cyclo-[R⁴CON(R⁵)—] may be represented by thehydrocarbylene radical (CR⁶R⁷)n, in other words, the formula:cyclo-[(CR⁶R⁷)_(n)CON(R⁵)—] wherein: the previously-stated values for(a) ratio of carbon to oxygen and (b) molecular weight apply; n is aninteger from 3 to 5; R⁵ is a saturated hydrocarbon radical containing 1to 12 carbon atoms; R⁶ and R⁷ are independently selected (for each n) bythe rules previously offered defining R¹⁻³. In the lactams representedby the formula: cyclo-[(CR⁶R⁷)_(n)CON(R⁵)—], all R⁶ and R⁷ arepreferably hydrogen, or contain a single saturated hydrocarbon radicalamong the n methylene units, and R⁵ is a saturated hydrocarbon radicalcontaining 3 to 12 carbon atoms. For example, 1-(saturated hydrocarbonradical)-5-methylpyrrolidin-2-ones. Representative amide compatibilizersinclude: 1-octylpyrrolidin-2-one, 1-decylpyrrolidin-2-one,1-octyl-5-methylpyrrolidin-2-one, 1-butylcaprolactam,1-cyclohexylpyrrolidin-2-one, 1-butyl-5-methylpiperid-2-one,1-pentyl-5-methylpiperid-2-one, 1-hexylcaprolactam,1-hexyl-5-methylpyrrolidin-2-one, 5-methyl-1-pentylpiperid-2-one,1,3-dimethylpiperid-2-one, 1-methylcaprolactam,1-butyl-pyrrolidin-2-one, 1,5-dimethylpiperid-2-one,1-decyl-5-methylpyrrolidin-2-one, 1-dodecylpyrrolid-2-one,N,N-dibutylformamide and N,N-diisopropylacetamide.

Compatibilizers of the present invention further comprise ketonesrepresented by the formula R¹COR², wherein R¹ and R² are independentlyselected from aliphatic, alicyclic and aryl hydrocarbon radicals havingfrom 1 to 12 carbon atoms, and wherein said ketones have a molecularweight of from about 70 to about 300 atomic mass units and a carbon tooxygen ratio of from about 4 to about 13. R¹ and R² in said ketones arepreferably independently selected from aliphatic and alicyclichydrocarbon radicals having 1 to 9 carbon atoms. The molecular weight ofsaid ketones is preferably from about 100 to 200 atomic mass units. Thecarbon to oxygen ratio in said ketones is preferably from about 7 toabout 10. R¹ and R² may together form a hydrocarbylene radical connectedand forming a five, six, or seven-membered ring cyclic ketone, forexample, cyclopentanone, cyclohexanone, and cycloheptanone. R¹ and R²may optionally include substituted hydrocarbon radicals, that is,radicals containing non-hydrocarbon substituents selected from halogens(e.g., fluorine, chlorine) and alkoxides (e.g. methoxy). R¹ and R² mayoptionally include heteroatom-substituted hydrocarbon radicals, that is,radicals which contain the atoms nitrogen (aza-), oxygen (keto-, oxa-)or sulfur (thia-) in a radical chain otherwise composed of carbon atoms.In general, no more than three non-hydrocarbon substituents andheteroatoms, and preferably no more than one, will be present for each10 carbon atoms in R¹ and R², and the presence of any suchnon-hydrocarbon substituents and heteroatoms must be considered inapplying the aforementioned ratio of carbon to oxygen and molecularweight limitations. Representative R¹ and R² aliphatic, alicyclic andaryl hydrocarbon radicals in the general formula R¹COR² include methyl,ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl,pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl,heptyl, octyl, nonyl, decyl, undecyl, dodecyl and their configurationalisomers, as well as phenyl, benzyl, cumenyl, mesityl, tolyl, xylyl andphenethyl. Representative ketone compatibilizers include: 2-butanone,2-pentanone, acetophenone, butyrophenone, hexanophenone, cyclohexanone,cycloheptanone, 2-heptanone, 3-heptanone, 5-methyl-2-hexanone,2-octanone, 3-octanone, diisobutyl ketone, 4-ethylcyclohexanone,2-nonanone, 5-nonanone, 2-decanone, 4-decanone, 2-decalone,2-tridecanone, dihexyl ketone and dicyclohexyl ketone.

Compatibilizers of the present invention further comprise nitrilesrepresented by the formula R¹CN, wherein R¹ is selected from aliphatic,alicyclic or aryl hydrocarbon radicals having from 5 to 12 carbon atoms,and wherein said nitriles have a molecular weight of from about 90 toabout 200 atomic mass units and a carbon to nitrogen ratio of from about6 to about 12. R¹ in said nitrile compatibilizers is preferably selectedfrom aliphatic and alicyclic hydrocarbon radicals having 8 to 10 carbonatoms. The molecular weight of said nitrile compatibilizers ispreferably from about 120 to about 140 atomic mass units. The carbon tonitrogen ratio in said nitrile compatibilizers is preferably from about8 to about 9. R¹ may optionally include substituted hydrocarbonradicals, that is, radicals containing non-hydrocarbon substituentsselected from halogens (e.g., fluorine, chlorine) and alkoxides (e.g.methoxy). R¹ may optionally include heteroatom-substituted hydrocarbonradicals, that is, radicals which contain the atoms nitrogen (aza-),oxygen (keto-, oxa-) or sulfur (thia-) in a radical chain otherwisecomposed of carbon atoms. In general, no more than three non-hydrocarbonsubstituents and heteroatoms, and preferably no more than one, will bepresent for each 10 carbon atoms in R¹, and the presence of any suchnon-hydrocarbon substituents and heteroatoms must be considered inapplying the aforementioned ratio of carbon to nitrogen and molecularweight limitations. Representative R¹ aliphatic, alicyclic and arylhydrocarbon radicals in the general formula R¹CN include include pentyl,isopentyl, neopentyl, tert-pentyl, cyclopentyl, cyclohexyl, heptyl,octyl, nonyl, decyl, undecyl, dodecyl and their configurational isomers,as well as phenyl, benzyl, cumenyl, mesityl, tolyl, xylyl and phenethyl.Representative nitrile compatibilizers include: 1-cyanopentane,2,2-dimethyl-4-cyanopentane, 1-cyanohexane, 1-cyanoheptane,1-cyanooctane, 2-cyanooctane, 1-cyanononane, 1-cyanodecane,2-cyanodecane, 1-cyanoundecane and 1-cyanododecane. Nitrilecompatibilizers are especially useful in compatibilizing HFCrefrigerants with aromatic and alkylaryl lubricants.

Compatibilizers of the present invention further comprise chlorocarbonsrepresented by the formula RCl_(x), wherein; x is selected from theintegers 1 or 2; R is selected from aliphatic and alicyclic hydrocarbonradicals having 1 to 12 carbon atoms; and wherein said chlorocarbonshave a molecular weight of from about 100 to about 200 atomic mass unitsand carbon to chlorine ratio from about 2 to about 10. The molecularweight of said chlorocarbon compatibilizers is preferably from about 120to 150 atomic mass units. The carbon to chlorine ratio in saidchlorocarbon compatibilizers is preferably from about 6 to about 7.Representative R aliphatic and alicyclic hydrocarbon radicals in thegeneral formula RCl_(x) include methyl, ethyl, propyl, isopropyl, butyl,isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl,tert-pentyl, cyclopentyl, cyclohexyl, heptyl, octyl, nonyl, decyl,undecyl, dodecyl and their configurational isomers. Representativechlorocarbon compatibilizers include: 3-(chloromethyl)pentane,3-chloro-3-methylpentane, 1-chlorohexane, 1,6-dichlorohexane,1-chloroheptane, 1-chlorooctane, 1-chlorononane, 1-chlorodecane, and1,1,1-trichlorodecane.

Compatibilizers of the present invention further comprise aryl ethersrepresented by the formula R¹OR², wherein: R¹ is selected from arylhydrocarbon radicals having from 6 to 12 carbon atoms; R² is selectedfrom aliphatic hydrocarbon radicals having from 1 to 4 carbon atoms; andwherein said aryl ethers have a molecular weight of from about 100 toabout 150 atomic mass units and a carbon to oxygen ratio of from about 4to about 20. The carbon to oxygen ratio in said aryl ethercompatibilizers is preferably from about 7 to about 10. RepresentativeR¹ aryl radicals in the general formula R¹OR² include phenyl, biphenyl,cumenyl, mesityl, tolyl, xylyl, naphthyl and pyridyl. Representative R²aliphatic hydrocarbon radicals in the general formula R¹OR² includemethyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl andtert-butyl. Representative aromatic ether compatibilizers include:methyl phenyl ether (anisole), 1,3-dimethyoxybenzene, ethyl phenyl etherand butyl phenyl ether.

Compatibilizers of the present invention further comprise1,1,1-trifluoroalkanes represented by the general formula CF₃R¹, whereinR¹ is selected from aliphatic and alicyclic hydrocarbon radicals havingfrom about 5 to about 15 carbon atoms, preferably primary, linear,saturated, alkyl radicals. Representative 1,1,1-trifluoroalkanecompatibilizers include: 1,1,1-trifluorohexane and1,1,1-trifluorododecane.

Compatibilizers of the present invention further comprise fluoroethersrepresented by the general formula R¹OCF₂CF₂H, wherein R¹ is selectedfrom aliphatic and alicyclic hydrocarbon radicals having from about 5 toabout 15 carbon atoms, preferably primary, linear, saturated, alkylradicals. Representative fluoroether compatibilizers include:C₈H₁₇OCF₂CF₂H and C₆H₁₃OCF₂CF₂H.

Compatibilizers of the present invention may comprise a singlecompatibilizer species or multiple compatibilizer species together inany proportion. For example, a compatibilizer may comprise a mixture ofcompounds from within a single compatibilizer species (e.g. a mixture ofpolyoxyalkylene glycol ethers) or a mixture of compounds chosen fromdifferent compatibilizer species (e.g. a mixture of a polyoxyalkyleneglycol ether with a ketone).

Compatibilizer of the present invention may optionally further comprisefrom about 1 to about 50 weight percent, preferably from about 1 toabout 10 weight percent based on total amount of compatibilizer, of anester containing the functional group —CO₂— and having a carbon to esterfunctional group carbonyl oxygen ratio of from about 2 to about 6. Theoptional esters may be represented by the general formula R¹CO₂R²,wherein R¹ and R² are independently selected from linear and cyclic,saturated and unsaturated, alkyl and aryl radicals. R¹ and R² areoptionally connected forming a ring, such as a lactone. Preferredoptional esters consist essentially of the elements C, H and O having amolecular weight of from about 80 to about 550 atomic mass units.Representative optional esters include:(CH₃)₂CHCH₂OOC(CH₂)₂₋₄OCOCH₂CH(CH₃)₂ (diisobutyl dibasic ester), ethylhexanoate, ethyl heptanoate, n-butyl proprionate, n-propyl proprionate,ethyl benzoate, di-n-propyl phthalate, benzoic acid ethoxyethyl ester,dipropyl carbonate, “Exxate 700” (a commercial C₇ alkyl acetate),“Exxate 800” (a commercial C₈ alkyl acetate), dibutyl phthalate, andt-butyl acetate.

Compatibilizer of the present invention may optionally further compriseat least one polyvinyl ether polymer, including polyvinyl etherhomopolymers, polyvinyl ether copolymers, and copolymers of vinyl etherswith hydrocarbon alkenes (e.g. ethylene and propylene), and/orfunctionalized hydrocarbon alkenes (e.g., vinyl acetate and styrene). Arepresentative polyvinyl ether is PVE 32, sold by Idemitsu Kosan andhaving a kinematic viscosity of 32 cs at 40° C.

Compatibilizers of the present invention may optionally further comprisefrom about 0.5 to about 50 weight percent (based on total amount ofcompatibilizer) of a linear or cyclic aliphatic or aromatic hydrocarboncontaining from 5 to 15 carbon atoms. Representative hydrocarbonsinclude pentane, hexane, octane, nonane, decane, Isopar® H (a highpurity C₁₁ to C₁₂ isoparaffinic), Aromatic 150 (a C₉ to C₁₁ aromatic),Aromatic 200 (a C₉ to C₁₅ aromatic) and Naptha 140. All of thesehydrocarbons are sold by Exxon Chemical, USA.

Compatibilizers of the present invention may optionally further containfrom about 0.01 to 30 weight percent (based on total amount ofcompatibilizer) of an additive which reduces the surface energy ofmetallic copper, aluminum, steel, or other metals found in heatexchangers in a way that reduces the adhesion of lubricants to themetal. Examples of metal surface energy reducing additives include thosedisclosed in WIPO PCT publication WO 96/7721, such as Zonyl® FSA, Zonyl®FSP and Zonyl® FSj, all products of E. I. du Pont de Nemours and Co. Inpractice, by reducing the adhesive forces between the metal and thelubricant (i.e. substituting for a compound more tightly bound to themetal), the lubricant circulates more freely through the heat exchangersand connecting tubing in an air conditioning or refrigeration system,instead of remaining as a layer on the surface of the metal. This allowsfor the increase of heat transfer to the metal and allows efficientreturn of lubricant to the compressor.

Commonly used refrigeration system additives may optionally be added, asdesired, to compositions of the present invention in order to enhancelubricity and system stability. These additives are generally knownwithin the field of refrigeration compressor lubrication, and includeanti wear agents, extreme pressure lubricants, corrosion and oxidationinhibitors, metal surface deactivators, free radical scavengers, foamcontrol agents, and the like. In general, these additives are presentonly in small amounts relative to the overall lubricant composition.They are typically used at concentrations of from less than about 0.1%to as much as about 3% of each additive. These additives are selected onthe basis of the individual system requirements. Some typical examplesof such additives may include, but are not limited to, lubricationenhancing additives, such as alkyl or aryl esters of phosphoric acid andof thiophosphates. These include members of the triaryl phosphate familyof EP lubricity additives, such as butylated triphenyl phosphates(BTPP), or other alkylated triaryl phosphate esters, e.g. Syn-0-Ad 8478from Akzo Chemicals, tricrecyl phosphates and related compounds.Additionally, the metal dialkyl dithiophosphates (e.g. zinc dialkyldithiophosphate or ZDDP, Lubrizol 1375) and other members of this familyof chemicals may be used in compositions of the present invention. Otherantiwear additives include natural product oils and assymetricalpolyhydroxyl lubrication additives such as Synergol TMS (InternationalLubricants). Similarly, stabilizers such as anti oxidants, free radicalscavengers, and water scavengers may be employed. Compounds in thiscategory can include, but are not limited to, butylated hydroxy toluene(BHT) and epoxides.

Compatiblizers such as ketones may have an objectionable odor which canbe masked by addition of an odor masking agent or fragrance. Typicalexamples of odor masking agents or fragrances may include Evergreen,Fresh Lemon, Cherry, Cinnamon, Peppermint, Floral or Orange Peel or soldby Intercontinental Fragrance, as well as d-limonene and pinene. Suchodor masking agents may be used at concentrations of from about 0.001%to as much as about 15% by weight based on the combined weight of odormasking agent and compatibilizer.

The present invention further comprises processes for producingrefrigeration comprising evaporating the present halogenatedhydrocarbon-containing refrigeration compositions in the vicinity of abody to be cooled, and processes for producing heat comprisingcondensing halogenated hydrocarbon refrigerant in the presence oflubricant and compatibilizer in the presence of a body to be heated.

The present invention further comprises processes for solubilizing ahalogenated hydrocarbon refrigerant in a lubricant, comprisingcontacting the halogenated hydrocarbon refrigerant with the lubricant inthe presence of an effective amount of compatibilizer, which forms asolution of the halogenated hydrocarbon refrigerant and the lubricant.

The present invention further relates to processes for returninglubricant from a non-compressor zone to a compressor zone in acompression refrigeration system comprising:

(a) contacting the lubricant in the non-compressor zone with at leastone halogenated hydrocarbon refrigerant in the presence of an effectiveamount of compatibilizer; and

(b) returning the lubricant from the noncompressor zone to thecompressor zone of the refrigeration system.

The present invention further comprises processes for returning alubricant from a low pressure zone to a compressor zone in arefrigeration system, comprising:

(a) contacting the lubricant in the low pressure zone of therefrigeration system with at least one halogenated hydrocarbonrefrigerant in the presence of an effective amount of compatibilizer;and

(b) returning the lubricant from the low pressure zone to the compressorzone of the refrigeration system.

EXAMPLES

The following examples are provided to illustrate certain aspects of thepresent invention, and are not intended to limit the scope of theinvention.

Herein, all percentages (%) are in weight percentages unless otherwiseindicated.

Naptha 140 (paraffins and cycloparaffins with normal boiling point of188-208° C.), Aromatic 150 (aromatics with normal boiling point 184-204°C.) and Isopar® H (isoparaffins with normal boiling point 161-203° C.)are all products of Exxon Chemicals. Exxate 700 is a C₇ alkyl acetateproduced by Exxon. “POE 22” is used herein as an abbreviation for MobilOil product Arctic EAL22, a polyol ester lubricant having a kinematicviscosity of 22 cs at 40° C. “POE 32” is used herein as an abbreviationfor Uniqema product Emkarate RL32, a polyol ester lubricant having akinematic viscosity of 32 cs at 40° C. Zerol 75 is an alkylbenzenelubricant having a kinematic viscosity of 15 cs at 40° C., Zerol 150 isan alkylbenzene lubricant having a kinematic viscosity of 32 cs at 40°C., Zerol 200 TD is an alkylbenzene lubricant having a kinematicviscosity of 40 cs at 40° C., and Zerol 300 is an alkylbenzene lubricanthaving a kinematic viscosity of 57 cs at 40° C. The Zerol® products aresold by the Shrieve Corporation. PVE 32 is a polyvinyl ether sold byIdemitsu Kosan having a kinematic viscosity of 32 cs at 40° C. UconLB-65 is a polyoxyproplyene glycol lubricant sold by Union Carbide withan average molecular weight of about 340. Ucon 50-HB-100 is a lubricantcontaining equal amounts of oxyethylene and oxpropylene groups sold byUnion Carbide with an average molecular weight of about 520. Ucon 488 isa Union Carbide product having a kinematic viscosity of 130 cs at 40° C.Suniso® 3GS (sometimes herein abbreviated as “3GS”) is a napthenicmineral oil with a kinematic viscosity of 33 cs at 40° C., Suniso® 4GS(sometimes herein abbreviated as “4GS”) is a napthenic mineral oil witha kinematic viscosity of 62 cs at 40° C. The Suniso® products are soldby Crompton Corporation. HAB 22 has a kinematic viscosity of 22 cs at40° C. and is a branched alkylbenzene oil sold by Nippon Oil.

HCFC-22 is chlorodifluoromethane. HFC-134a is 1,1,1,2-tetrafluoroethane.R401A is a refrigerant blend containing 53 wt % HCFC-22, 13 wt %HFC-152a (1,1-difluoroethane) and 34 wt % HCFC-124(2-chloro-1,1,1,2-tetrafluoroethane). R404A is a refrigerant blendcontaining 44 wt % HFC-125 (pentafluoroethane), 52 wt % HFC-143a(1,1,1-trifluoroethane) and 4 wt % HFC-134a. R407C is a refrigerantblend containing 23 wt % HFC-32 (difluoromethane), 25 wt % HFC-125 and52 wt % HFC-134a. R410A is a refrigerant blend containing 50 wt % HFC-32and 50 wt % HFC-125.

Abbreviations used herein for a number of materials are shown in thetable below with the corresponding material name, and if relevant,formula and molecular weight:

Abbre- Molec- vi- ular ation Material Formula Weight BnB Butylene glycolC₄H₉OCH₂CHOHCH₂CH₃ 146 n-butyl ether PnB Propylene glycolC₄H₉OCH₂CHOHCH₃ 132 n-butyl ether DPnB Dipropylene glycolC₄H₉O[CH₂CH(CH₃)O]₂H 190 n-butyl ether TPnB Tripropylene glycolC₄H₉O[CH₂CH(CH₃)O]₃H 248 n-butyl ether PnP Propylene glycolC₃H₇OCH₂CHOHCH₃ 118 n-propyl ether DPnP Dipropylene glycolC₃H₇O[CH₂CH(CH₃)O]₂H 176 n-propyl ether DPM Dipropylene glycolCH₃O[CH₂CH(CH₃)O]₂H 148 methyl ether DMM Dipropylene glycolCH₃O[CH₂CH(CH₃)O]₂CH₃ 162 dimethyl ether PGH Propylene glycolC₆H₁₃OCH₂CHOHCH₃ 160 hexyl ether EGO Ethylene glycol octylC₈H₁₇OCH₂CH₂OH 174 ether PTB Propylene glycol C(CH₃)₃OCH(CH₃)CH₂OH 132t-butyl ether 1,5- 1,5-dimethyl C₇H₁₃NO 127 DMPD piperidone DMPD Mixtureof 70 wt % C₇H₁₃NO 127 1,3- and 30 wt % 1,5-dimethyl piperid- 2-one OP1-octyl pyrrolidin- C₁₂H₂₃NO 197 2-one DBE-IB Diisobutyl dibasic(CH₃)₂CHCH₂OOC(CH₂)₂- 242 esters (e.g. diisobutyl ₄OCOCH₂CH(CH₃)₂ avg.esters of succinic, glu- taric and adipic acids)

Example 1

Polyoxyalkylene glycol ether compatibilizers of the present inventionwere placed in a suitable container with refrigerant and lubricant andthe temperature was lowered until two phases were observed to the nakedeye (i.e., the phase separation temperature, also herein referred to as“PST”). The composition in the container was 50 wt % HFC-134a, 25 wt %Zerol 150 and 25 wt % of compatibilizer. Results are shown below, and inFIG. 1.

Example 1

Phase Separation Temper- Carbon/ ature Oxygen Compatibilizer Formula (°C.) Ratio Ethylene glycol butyl ether C₆H₁₄O₂  4 3.0 Ethylene glycoldiethyl ether C₆H₁₄O₂  5 3.0 Ethylene glycol hexyl ether C₁₀H₂₂O₂ 26 4.0Dipropylene glycol methyl ether C₇H₁₆O₃ 27 2.33 Dipropylene glycolpropyl ether C₉H₂₀O₃   5.5 3.0 Propylene glycol butyl ether C₇H₁₆O₂  63.5 Propylene glycol propyl ether C₆H₁₄O₂ 11 3.0 Tripropylene glycolbutyl ether C₁₃H₂₈O₄ 11 3.25 Propylene glycol dimethyl ether C₅H₁₂O₂ 122.5 Tripropylene glycol propyl ether C₁₂H₂₆O₄ 12 3.0 Dipropylene glycoldimethyl ether C₈H₁₈O₃ 13 2.67 Dipropylene glycol butyl ether C₁₀H₂₂O₃13 3.33 Diethylene glycol butyl ether C₈H₁₈O₃ 13 2.7 Butylene glycoln-butyl ether C₈H₁₈O₂ 16 4 Dibutylene glycol n-butyl ether C₁₂H₂₆O₃ 18 4Propylene glycol t-butyl ether C₇H₁₆O₂ 20 3.5 Comparative DataTetraethylene glycol dimethyl ether C₁₀H₂₂O₅ 32 2.0 Ucon LB-65polyalkylene 28 3.0 glycol Ucon 50-HB-100 polyalkylene 32 2.5 glycol PVE32 polyvinyl ether 62 5 Dipropylene glycol C₆H₁₄O₃ not 2 miscible withZerol 150The data show significantly lower phase separation temperatures versus50 wt % HFC-134a/50 wt % Zerol 150 alkylbenzene lubricant which has aphase separation temperature of 137° C. The data show that a minimumphase separation temperature occurs at a specific carbon to oxygen ratioof the polyoxyalkylene glycol ether compatibilizer indicating maximumsolubility improvement of hydrofluorocarbon refrigerant in alkylbenzenelubricant.

Example 2

Polyoxyalkylene glycol ether compatibilizers of the present inventionwere placed in a suitable container with refrigerant and lubricant andthe temperature lowered until two phases were observed. The compositionin the container was 50 wt % R401A refrigerant, 40 wt % Suniso 3GS and10 wt % of a polyoxyalkylene glycol ether compatibilizer. Results areshown below, and in FIG. 2.

Example 2

Phase Separation Temper- Carbon/ ature Oxygen Compatibilizer Formula (°C.) Ratio Propylene glycol hexyl ether C₉H₂₀O₂ −26 4.5 Butylene glycolbutyl ether C₈H₁₈O₂ −19 4.0 Ethylene glycol octyl ether C₁₀H₂₂O₂ −18 5.0Propylene glycol butyl ether C₇H₁₆O₂  −7 3.5 Dipropylene glycol C₁₀H₂₂O₃−11 3.33 butyl ether Tripropylene glycol butyl ether C₁₃H₂₈O₄  −7 3.25Comparative Data Tetraglyme C₁₀H₂₂O₅ not miscible 2.0 with 3GSThe data show significantly lower phase separation temperature versus 50wt % R401A refrigerant/50 wt % Suniso 3GS mineral oil, which has a phaseseparation temperature of 24° C. The data show that a minimum phaseseparation temperature occurs at a specific carbon to oxygen ratio ofthe polyoxyalkylene glycol ether compatibilizer, indicating maximumsolubility improvement of hydrochlorofluorocarbon-containing refrigerantin mineral oil lubricant.

Butyl phenyl ether (C₁₀H₁₄O), an aryl ether compatibilizer, was alsomeasured and showed a surprisingly low phase separation temperature of−32° C.

Example 3

Ketone compatibilizers of the present invention were placed in asuitable container with refrigerant and lubricant and the temperaturelowered until two phases were observed. The composition in the containerwas 50 wt % HFC-134a, 25 wt % Zerol 150 and 25 wt % of a ketonecompatibilizer. Results are shown below, and in FIG. 3.

Example 3

Phase Separation Carbon/ Temperature Oxygen Compatibilizer Formula (°C.) Ratio Cycloheptanone C₇H₁₂O −24 7 2-Nonanone C₉H₁₈O −22 9 3-OctanoneC₈H₁₆O −17 8 Cyclohexanone C₆H₁₀O −16 6 2-Heptanone C₇H₁₄O −15 72-Decanone C₁₀H₂₀O −15 10  4-Decanone C₁₀H₂₀O −14 10  2-Octanone C₈H₁₆O−12 8 5-Nonanone C₉H₁₈O −12 9 4-Ethylcyclohexanone C₈H₁₄O −12 83-Heptanone C₇H₁₄O  −8 7 Diisobutyl ketone C₉H₁₈O  −4 9 2-DecaloneC₁₀H₁₆O    2 10  Methyl propyl ketone C₅H₁₀O    3 5 Acetophenone C₈H₈O   4 8 Butyrophenone C₁₀H₁₂O    8 10  2-tridecanone C₁₃H₂₆O    8 13 Methyl ethyl ketone C₄H₈O   16 4 Dihexylketone C₁₃H₂₆O   21 13 Hexanophenone C₁₃H₁₈O   28 13  Dicyclohexyl ketone C₁₃H₂₂O   53 13 Comparative Data Acetone C₃H₆O   56 3

The data show significantly lower phase separation temperatures versus50 wt % HFC-134a/50 wt % Zerol 150 alkylbenzene lubricant which has aphase separation temperature of 137° C. The data show that a minimumphase separation temperature occurs at a specific carbon to oxygen ratioof the ketone compatibilizer indicating maximum solubility improvementof hydrofluorocarbon refrigerant in alkylbenzene lubricant.

Example 4

Nitrile compatibilizers of the present invention were placed in asuitable container with refrigerant and lubricant and the temperaturelowered until two phases were observed. The composition in the containerwas 50 wt % HFC-134a, 25 wt % Zerol 150 and 25 wt % of a nitrilecompound. Results are shown below, and in FIG. 4.

Example 4

Phase Separation Carbon/ Temperature Nitrogen Compatibilizer Formula (°C.) Ratio 1-cyanooctane C₉H₁₇N −26 9 2-cyanooctane C₉H₁₇N −23 91-cyanoheptane C₈H₁₅N −18 8 1-cyanodecane C₁₁H₂₁N −13 11  2-cyanodecaneC₁₁H₂₁N −12 11  1-cyanopentane C₆H₁₁N  −3 6 1-cyanoundecane C₁₂H₂₃N    312 

The data show significantly lower phase separation temperatures versus50 wt % HFC-134a/50 wt % Zerol 150 alkylbenzene lubricant which has aphase separation temperature of 137° C. The data show that a minimumphase separation temperature occurs at a specific carbon to nitrogenratio of the nitrile compatibilizer indicating solubility improvement ofhydrofluorocarbon refrigerant in alkylbenzene lubricant.

Example 5

Chlorocarbon compatibilizers of the present invention were placed in asuitable container with refrigerant and lubricant and the temperaturelowered until two phases were observed. The composition in the containerwas 50 wt % HFC-134a, 25 wt % Zerol 150 and 25 wt % of a chlorocarboncompatibilizer. Results are shown below, and in FIG. 5.

Example 5

Phase Separation Carbon/ Temperature Chlorine Compatibilizer Formula (°C.) Ratio 1-chlorobutane C₄H₉Cl 16 4 3-(chloromethyl)pentane C₆H₁₃Cl 346 1-chloroheptane C₇H₁₅Cl 40 7 1,6-dichlorohexane C₆H₁₂Cl₂ 47 31-chlorooctane C₈H₁₇Cl 54 8 1-chlorohexane C₆H₁₃Cl 38 63-chloro-3-methylpentane C₆H₁₃Cl 23 6

The data show significantly lower phase separation versus 50 wt %HFC-134a/50 wt % Zerol 150 alkylbenzene lubricant which has a phaseseparation temperature of 137° C. The data show that a minimum phaseseparation temperature occurs at a specific carbon to chlorine ratio ofthe chlorocarbon compatibilizer indicating maximum solubilityimprovement of hydrofluorocarbon refrigerant in alkylbenzene lubricant.

Example 6

Chlorocarbon compatibilizers of the present invention were placed in asuitable container with refrigerant and lubricant and the temperaturelowered until two phases were observed. The composition in the containerwas 50 wt % R401A refrigerant, 40 wt % Suniso 3GS and 10 wt %chlorocarbon compatibilizer. Results are shown below and in FIG. 6.

Example 6

Phase Separation Carbon/ Temperature Chlorine Compatibilizer Formula (°C.) Ratio 3-(chloromethyl)pentane C₆H₁₃Cl −25 6 1-chloroheptane C₇H₁₅Cl−24 7 C₆&C₈ monochlorides, — −17 6-8 1:2 weight ratio 1,6-dichlorohexaneC₆H₁₂Cl₂ −14 3 1-chlorooctane C₈H₁₇Cl −13 8 1-chlorohexane C₆H₁₃Cl −10 63-chloro-3-methylpentane C₆H₁₃Cl −10 6 1-chlorononane C₉H₁₉Cl  −7 9

The data show significantly lower phase separation versus 50 wt % R401Arefrigerant/50 wt % Suniso 3GS mineral oil which has a phase separationtemperature of 24° C. The data show that a minimum phase separationtemperature occurs at a specific carbon to chlorine ratio of thechlorocarbon compatibilizer indicating maximum solubility ofhydrochlorofluorocarbon-containing refrigerant in mineral oil lubricant.

Example 7

Amide compatibilizers of the present invention were placed in a suitablecontainer with refrigerant and lubricant and the temperature lowereduntil two phases were observed. The composition in the container waseither HFC-134a or R401A refrigerants, Zerol 150 or Suniso 3GSlubricants, and an amide compatibilizer. Results are shown below and inFIGS. 7 and 8.

Example 7

PST (° C.) 25% PST Zerol (° C.) 150 40% 25% 3GS Com- 10% Car- pati- Com-bon bilizer pati- to 50% bilizer Oxy- HFC- 50% gen CompatibilizerFormula 134a R401A Ratio 1-octyl pyrrolidin-2-one C₁₂H₂₃NO −25 −34 121-heptyl-5-methylpyrrolidin-2-one C₁₂H₂₃NO −18 — 12 1-octyl-5-methylpyrrolidin-2-one C₁₃H₂₅NO −17 — 13 1-butylcaprolactam C₁₀H₁₉NO −17 — 101-cyclohexylpyrrolidin-2-one C₁₀H₁₇NO −15 −27 101-butyl-5-methylpiperidone C₁₀H₁₉NO −13 −20 10 1-pentyl-5-methylpiperidone C₁₁H₂₁NO −10 −25 11 1-hexyl caprolactam C₁₂H₂₃NO −10 — 121-hexyl-5-methylpyrrolidin-2-one C₁₁H₂₁NO −10 — 11 1,3-dimethylpiperidone C₇H₁₃NO  −9 —  7 DMPD C₇H₁₃NO  −6 —  71-decyl-2-pyrrolidin-2-one C₁₄H₂₇NO  −4 — 14 1,1-dibutylformamideC₉H₁₉NO  −2 −16  9 1-methyl caprolactam C₇H₁₃NO  −1 −31  7 1-butylpyrrolidin-2-one C₈H₁₅NO  −1  −4  8 1-decyl-5-methylpyrrolidin-2-oneC₁₅H₂₉NO    2 — 15 1,5-dimethyl piperidone C₇H₁₃NO    2 −15  7 1-dodecylpyrrolidin-2-one C₁₆H₃₁NO    8 −38 16 1,1-diisopropyl acetamide C₈H₁₇NO  13    4  8

The data show significantly lower phase separation temperatures for bothhydrofluorocarbon and hydrochlorofluorocarbon-containingrefrigerant/lubricant systems versus 50 wt % HFC-134a/50 wt % Zerol 150which has a phase separation temperature of 137° C., and 50 wt % R401Arefrigerant/50 wt % Suniso 3GS which has a phase separation temperatureof 24° C. The minimum phase separation temperature for amidecompatibilizers with HFC-134a and Zerol 150 occurs at a specific carbonto amide oxygen ratio indicating a maximum solubility improvement forhydrofluorocarbon refrigerants and alkylbenzene lubricant. The phaseseparation temperature for amide compatibilizers with R401A refrigerantand Suniso 3GS mineral oil lubricant decreases with increasing carbon toamide oxygen ratio.

Example 8

Polyoxyalkylene glycol ether compatibilizers of the present inventionwere placed in a suitable container with refrigerant and lubricant andthe temperature was lowered until two phases were observed. Thecomposition in the container was 25 wt % Zerol 150, 25 wt % ofcompatibilizer and 50% of either HFC-32, HFC-125 or R410A refrigerants.Results are shown below, and in FIG. 9.

Example 8

Carbon/ PST with PST with PST with Oxygen Compatibilizer Formula HFC-32(° C.) HFC-125 (° C.) R410A (° C.) Ratio Ethylene glycol dimethyl etherC₄H₁₀O₂ 29 27  12 2.0 Propylene glycol dimethyl ether C₅H₁₂O₂ 23 7 6 2.5Ethylene glycol diethyl ether C₆H₁₄O₂ 16 3 −1 3.0 Propylene glycol butylether C₇H₁₆O₂ 25 2 9 3.5 Butylene glycol n-butyl ether C₈H₁₈O₂ — 6 — 4  The data show an unexpected and generally lower phase separationtemperature when HFC-32 and HFC-125 refrigerants are combined to formR410A refrigerant versus neat HFC-32 or HFC-125.

Example 9

Aryl ether, 1,1,1-trifluoroalkane and fluoroether compatibilizers of thepresent invention were placed in a suitable container with refrigerantand lubricant and the temperature lowered until two phases wereobserved. The composition in the container was 50 wt % HFC-134arefrigerant, 25 wt % Zerol 150 alkylbenzene lubricant and 25 wt % ofcompatibilizer. Results are shown below.

Example 9

PST (° C.) PST (° C.) 25% Zerol 150 40% 3GS 25% 10% CompatibilizerCompatibilizer Compatibilizer Formula 50% HFC-134a 50% R401Amethoxybenzene C₇H₈O 13 — 1,3-dimethoxybenzene C₈H₁₀O₂ 15 —ethoxybenzene C₈H₁₀O 20 — 1,1,1-trifluorododecane C₁₂H₂₃F₃ 27 −281,1,1-trifluorohexane C₆H₁₁F₃ 32 — C₈H₁₇OCF₂CF₂H C₁₀H₁₈F₄O 21 −12C₆H₁₃OCF₂CF₂H C₈H₁₄F₄O 27 −11The data show significantly lower phase separation temperatures forthese compatibilizers with both hydrofluorocarbon andhydrochlorofluorocarbon-containing refrigerants versus 50 wt %HFC-134a/50 wt % Zerol 150, which has a phase separation temperature of137° C., and 50 wt % R401A refrigerant/50 wt % Suniso 3GS, which has aphase separation temperature of 24° C.

Examples 10-28

A test tube was filled with 7.5 grams of HFC-43-10 mee(CF₂CF₂CHFCHFCF₃), herein referred to as “4310”, and 2.5 grams ofselected lubricant. Compatibilizers of the present invention were addedin 1 gram increments to the 4310/lubricant mixture and the contents ofthe tube were agitated at 25° C. Changes in phase levels were recordedand compositions of layers analyzed by gas chromatography. One gramincrements of compatibilizer were added until the contents of the tubereached one homogeneous phase. Results are shown below.

Example 10

Grams of Total Bottom DPM added Composition in Top Layer Layer Top LayerBottom Layer to Tube Tube Height, mm Height, mm wt % wt % 0 75.0% 431020 35 — — 25.0% Zerol 150 1 9.1% DPM 21 41 5% DPM 11% DPM 68.2% 4310 7%4310 85% 4310 22.7% Zerol 150 88% Zerol 150 4% Zerol 150 2 16.7% DPM 2049 9% DPM 21% DPM 62.5% 4310 9% 4310 73% 4310 20.8% Zerol 150 82% Zerol150 6% Zerol 150 3 23.1% DPM 18 59 10% DPM 29% DPM 57.7% 4310 7% 431063% 4310 19.2% Zerol 150 83% Zerol 150 8% Zerol 150 4 28.6% DPM 14 7118% DPM 35% DPM 53.6% 4310 11% 4310 53% 4310 17.8% Zerol 150 71% Zerol150 12% Zerol 150 5 33.3% DPM  5 87 24% DPM 37% DPM 50.0% 4310 14% 431045% 4310 16.7% Zerol 150 62% Zerol 150 18% Zerol 150 6 37.5% DPM — — onelayer one layer 46.9% 4310 15.6% Zerol 150

Example 11

Grams of Total Bottom PnB added Composition in Top Layer Layer Top LayerBottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0% 431021 34 — — 25.0% Zerol 150 1 9.1% D PnB 23 40 19% PnB 8% PnB 68.2% 431015% 4310 89% 4310 22.7% Zerol 150 66% Zerol 150 3% Zerol 150 2 16.7% PnB25 47 31% PnB 17% PnB 62.5% 4310 25% 4310 79% 4310 20.8% Zerol 150 44%Zerol 150 4% Zerol 150 3 23.1% PnB 23 57 35% PnB 25% PnB 57.7% 4310 35%4310 69% 4310 19.2% Zerol 150 30% Zerol 150 6% Zerol 150 4 28.6% PnB — —one layer one layer 53.6% 4310 17.8% Zerol 150

Example 12

Grams of Total Bottom DPnB added Composition in Top Layer Layer TopLayer Bottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 34 — — 25.0% Zerol 150 1 9.1% DPnB 23 40 14% DPnB 7% DPnB 68.2%4310 13% 4310 88% 4310 22.7% Zerol 150 72% Zerol 150 5% Zerol 150 216.7% DPnB 26 45 25% DPnB 15% DPnB 62.5% 4310 18% 4310 79% 4310 20.8%Zerol 150 57% Zerol 150 6% Zerol 150 3 23.1% DPnB 27 51 35% DPnB 24%DPnB 57.7% 4310 29% 4310 68% 4310 19.2% Zerol 150 36% Zerol 150 8%Zerol150 4 28.6% DPnB — — one layer one layer 53.6% 4310 17.8% Zerol 150

Example 13

Grams of Total Bottom TPnB added Composition in Top Layer Layer TopLayer Bottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 34 — — 25.0% Zerol 150 1 9.1% TPnB 24 40 29% TPnB 6% TPnB 68.2%4310 23% 4310 93% 4310 22.7% Zerol 150 48% Zerol 150 1% Zerol 150 216.7% TPnB 27 44 33% TPnB 14% TPnB 62.5% 4310 25% 4310 84% 4310 20.8%Zerol 150 42% Zerol 150 2% Zerol 150 3 23.1% TPnB 30 48 32% TPnB 19%TPnB 57.7% 4310 33% 4310 77% 4310 19.2% Zerol 150 35% Zerol 150 4%Zerol150 4 28.6% TPnB — — one layer one layer 53.6% 4310 17.8% Zerol 150

Example 14

Grams of Total Bottom PnP added Composition in Top Layer Layer Top LayerBottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0% 431021 34 — — 25.0% Zerol 150 1 9.1% PnP 21 41 17% PnP 9% PnP 68.2% 4310 15%4310 89% 4310 22.7% Zerol 150 68% Zerol 150 2% Zerol 150 2 16.7% PnP 2348 27% PnP 18% PnP 62.5% 4310 22% 4310 74% 4310 20.8% Zerol 150 51%Zerol 150 8% Zerol 150 3 23.1% PnP 20 59 29% PnP 26% PnP 57.7% 4310 25%4310 68% 4310 19.2% Zerol 150 46% Zerol 150 6% Zerol 150 4 28.6% PnP — —one layer one layer 53.6% 4310 17.8% Zerol 150

Example 15

Grams of Total Bottom DPnP added Composition in Top Layer Layer TopLayer Bottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 34 — — 25.0% Zerol 150 1 9.1% DPnP 22 41 8% DPnP 8% DPnP 68.2%4310 7% 4310 87% 4310 22.7% Zerol 150 85% Zerol 150 5% Zerol 150 2 16.7%DPnP 23 47 16% DPnP 17% DPnP 62.5% 4310 12% 4310 76% 4310 20.8% Zerol150 72% Zerol 150 7% Zerol 150 3 23.1% DPnP 22 56 27% DPnP 24% DPnP57.7% 4310 19% 4310 67% 4310 19.2% Zerol150 54% Zerol 150 9% Zerol150 428.6% DPnP — — one layer one layer 53.6% 4310 17.8% Zerol 150

Example 16

Grams of Total Bottom DMM added Composition in Top Layer Layer Top LayerBottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0% 431021 34 — — 25.0% Zerol 150 1 9.1% DMM 22 40 8% DMM 9% DMM 68.2% 4310 11%4310 90% 4310 22.7% Zerol 150 81% Zerol 150 1% Zerol 150 2 16.7% DMM 2347 16% DMM 16% DMM 62.5% 4310 14% 4310 82% 4310 20.8% Zerol 150 70%Zerol 150 2% Zerol 150 3 23.1% DMM 22 55 24% DMM 21% DMM 57.7% 4310 21%4310 72% 4310 19.2% Zerol 150 55% Zerol 150 7% Zerol 150 4 28.6% DMM  481 33% DMM 29% DMM 53.6% 4310 37% 4310 55% 4310 17.8% Zerol 150 30%Zerol 150 16% Zerol 150 5 33.3% DMM — — one layer one layer 50.0% 431016.7% Zerol 150

Example 17

In this example, DIP=equal parts by weight of PnB, DPnB and Isopar H.

Total Bottom Grams of DIP Composition in Top Layer Layer Top LayerBottom Layer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 34 — — 25.0% Zerol 150 1 3.0% PnB 26 37 6% PnB 3% PnB 3.0% 16%1% Isopar(R)H Isopar(R)H Isopar(R)H 3% DPnB 3.0% DPnB 6% DPnB 91% 431068.2% 4310 17% 4310 2% Zerol 150 22.7% Zerol 150 55% Zerol 150 2 5.6%PnB 30 41 11% PnB 5% PnB 5.6% 24% 2% Isopar(R)H Isopar(R)H Isopar(R)H 5%DPnB 5.6% DPnB 11% DPnB 86% 4310 62.5% 4310 29% 4310 2% Zerol 150 20.8%Zerol 150 25% Zerol 150 3 7.7% PnB 36 43 11% PnB 7% PnB 7.7% 19% 4%Isopar(R)H Isopar(R)H Isopar(R)H 8% DPnB 7.7% DPnB 11% DPnB 77% 431057.7% 4310 29% 4310 4% Zerol 150 19.2% Zerol 150 30% Zerol 150 4 9.5%PnB 44 44 10% PnB 9% PnB 9.5% 14% 7% Isopar(R)H Isopar(R)H Isopar(R)H10% DPnB 9.5% DPnB 11% DPnB 64% 4310 53.6% 4310 30% 4310 10% Zerol 15017.8% Zerol 150 35% Zerol 150 5 11.1% PnB — — one layer one layer 11.1%Isopar(R)H 11.1% DPnB 50.0% 4310 16.7% Zerol 150

Example 18

In this example, 2-heptanone is referred to as “A”.

Total Bottom Grams of A Composition in Top Layer Layer Top Layer BottomLayer added to Tube in Tube Height, mm Height, mm wt % Wt % 0 75.0% 431019 34 25.0% 3GS 1 9.1% A 20 42 3.2% A 9.8% A 68.2% 4310 3.2% 4310 86.4%4310 22.7% 3GS 92.9% 3GS 3.8% 3GS 2 16.7% A 19 52 7.6% A 16.9% A 62.5%4310 6.7% 4310 77.7% 4310 20.8% 3GS 85.7% 3GS 5.4% 3GS 3 23.1% A 15 6410.8% A 23.2% A 57.7% 4310 10.6% 4310 63.7% 4310 19.2% 3GS 78.6% 3GS13.1% 3GS 4 28.6% A one layer one layer 53.6% 4310 17.8% 3GS

Example 19

In this example, 5-methyl-2-hexanone is referred to as “A”. Grams of Aadded Total Heights Composition- Composition - to Composition of bothtop bottom Tube in Tube layer layer layer 0 75% 4310 Top - 19 mm — — 25%3GS Bottom - 34 mm 1 9.1% A Top - 3.0% A 10.3% A 68.2% 4310 21 mm, clear3.4% 4310 87.9% 4310 22.7% 3GS Bottom - 93.6% 3GS 1.8% 3GS 42 mm, clear2 16.7% A Top - 8.9% A 18.2% A 62.5% 4310 19 mm, clear 6.9% 4310 78.6%4310 20.8% 3GS Bottom - 84.2% 3GS 3.2% 3GS 51 mm, clear 3 23.1% A Top -10.8% A 23.7% A 57.7% 4310 16 mm, clear 7.9% 4310 62.9% 4310 19.2% 3GSBottom - 81.3% 3GS 13.4% 3GS 62 mm, clear 4 28.6% A Top - 13.6% A 25.8%A 53.6% 4310 10 mm, clear 9.9% 4310 59.2% 4310 17.8% 3GS Bottom - 76.5%3GS 15.0% 3GS 78 mm, clear   4.5 31.0% A Top - 27.0% A 29.8% A 51.7%4310 3 mm, clear 14.1% 4310 50.0% 4310 17.3% 3GS Bottom - 58.9% 3GS20.2% 3GS 90 mm, clear 5 33.3% A Clear one — — 50.0% 4310 layer - 16.7%3GS 97 mm

Example 20

Grams of Total Bottom Isopar H added Composition in Top Layer Layer TopLayer Bottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 19 34 — — 25.0% 3GS 1 9.1% 29 34 31.4% 5.4% Isopar(R)H Isopar(R)HIsopar(R)H 68.2% 4310 0.4% 4310 93.9% 4310 22.7% 3GS 68.2% 3GS 0.7% 3GS2 16.7% 37 34 45.7% 8.2% Isopar(R)H Isopar(R)H Isopar(R)H 62.5% 43101.0% 4310 90.7% 4310 20.8% 3GS 53.3% 3GS 1.0% 3GS 3 23.1% 46 34 56.8%9.5% Isopar(R)H Isopar(R)H Isopar(R)H 57.7% 4310 1.9% 4310 89.6% 431019.2% 3GS 41.3% 3GS 0.9% 3GS 4 28.6% 57 33 62.9% 10.5% Isopar(R)HIsopar(R)H Isopar(R)H 53.6% 4310 2.9% 4310 88.6% 4310 17.8% 3GS 34.2%3GS 0.9% 3GS 5 33.3% 66 33 69.0% 11.6% Isopar(R)H Isopar(R)H Isopar(R)H50.0% 4310 3.3% 4310 87.7% 4310 16.7% 3GS 27.7% 3GS 0.7% 3GS 10  NeverReached — — — — one phase

Example 21

In this example, PDD=equal parts by weight of PnB, DMM and DPnB.

Total Bottom Grams of PDD Composition in Top Layer Layer Top LayerBottom Layer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 34 — — 25.0% Zerol 150 1 3.0% PnB 23 39 5% PnB 3% PnB 3.0% DMM4% DMM 3% DMM 3.0% DPnB 5% DPnB 3% DPnB 68.2% 4310 14% 4310 87% 431022.7% Zerol 150 72% Zerol 150 4% Zerol 150 2 5.6% PnB 24 46 6% PnB 6%PnB 5.6% DMM 5% DMM 6% DMM 5.6% DPnB 6% DPnB 6% DPnB 62.5% 4310 15% 431076% 4310 20.8% Zerol 150 68% Zerol 150 6% Zerol 150 3 7.7% PnB 23 55 11%PnB 8% PnB 7.7% DMM 10% DMM 9% DMM 7.7% DPnB 11% DPnB 8% DPnB 57.7% 431024% 4310 63% 4310 19.2% Zerol 150 44% Zerol 150 12% Zerol 150 4 11.1%PnB — — one layer one layer 11.1% DMM 11.1% DPnB 50.0% 4310 16.7% Zerol150

Example 22

In this example, DDN=equal parts by weight of DPnB, DMM and Naptha 140(“N140”).

Total Bottom Grams of DDN Composition in Top Layer Layer Top LayerBottom Layer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 34 — — 25.0% Zerol 150 1 3.0% DPnB 25 38 3% DPnB 3% DPnB 3.0%DMM 3% DMM 3% DMM 3.0% N140 9% N140 <1% N140 68.2% 4310 8% 4310 93% 431022.7% Zerol 150 77% Zerol 150 1% Zerol 150 2 5.6% DPnB 29 42 7% DPnB 5%DPnB 5.6% DMM 6% DMM 5% DMM 5.6% N140 16% N140 1% N140 62.5% 4310 12%4310 87% 4310 20.8% Zerol 150 59% Zerol 150 2% Zerol 150 3 7.7% DPnB 3445 9% DPnB 7% DPnB 7.7% DMM 8% DMM 8% DMM 7.7% N140 19% N140 3% N14057.7% 4310 17% 4310 80% 4310 19.2% Zerol 150 47% Zerol 150 2% Zerol 1504 9.5% DPnB 39 48 10% DPnB 9% DPnB 9.5% DMM 9% DMM 10% DMM 9.5% N140 18%N140 5% N140 53.6% 4310 23% 4310 70% 4310 17.8% Zerol 150 40% Zerol 1506% Zerol 150 5 11.1% DPnB 43 52 11% DPnB 11% DPnB 11.1% DMM 11% DMM 11%DMM 11.1% N140 15% N140 9% N140 50.0% 4310 39% 4310 58% 4310 16.7% Zerol150 24% Zerol 150 11% Zerol 150 6 12.5% DPnB — — One Layer One Layer12.5% DMM 12.5% N140 46.9% 4310 15.6% Zerol 150

Example 23

In this example, DDA=equal parts by weight of DPnB, DMM and Aromatic 150(“A150”).

Total Bottom Grams of DDA Composition in Top Layer Layer Top LayerBottom Layer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 34 — 25.0% Zerol 150 1 3.0% DPnB 24 38 5% DPnB 2% DPnB 3.0% DMM4% DMM 2% DMM 3.0% A150 13% A150 1% A150 68.2% 4310 18% 4310 93% 431022.7% Zerol 150 60% Zerol 150 2% Zerol 150 2 5.6% DPnB 28 42 6% DPnB 5%DPnB 5.6% DMM 5% DMM 5% DMM 5.6% A150 12% A150 2% A150 62.5% 4310 17%4310 86% 4310 20.8% Zerol 150 60% Zerol 150 2% Zerol 150 3 7.7% DPnB 3246 11% DPnB 7% DPnB 7.7% DMM 10% DMM 8% DMM 7.7% A150 20% A150 4% A15057.7% 4310 36% 4310 77% 4310 19.2% Zerol 150 23% Zerol 150 4% Zerol 1504 9.5% DPnB 35 51 12% DPnB 9% DPnB 9.5% DMM 12% DMM 9% DMM 9.5% A150 18%A150 7% A150 53.6% 4310 40% 4310 68% 4310 17.8% Zerol 150 18% Zerol 1507% Zerol 150 5 11.1% DPnB — — One Layer One Layer 11.1% DMM 11.1% A15050.0% 4310 16.7% Zerol 150

Example 24

In this example, PD=2 parts by wt PnB, 1 part DPnB.

Total Bottom Grams of PD Composition in Top Layer Layer Top Layer BottomLayer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0% 4310 2134 — — 25.0% Zerol 150 1 9.1% PD 23 39 8%PnB 5%PnB 68.2% 4310 4% DPnB 2%DPnB 22.7% Zerol 150 12% 4310 91% 4310 76% Zerol 150 2% Zerol 150 216.7% PD 25 44 14% PnB 10% PnB 62.5% 4310 7% DPnB 5% DPnB 20.8% Zerol150 20% 4310 82% 4310 59% Zerol 150 3% Zerol 150 3 23.1% PD 26 52 24%PnB 15% PnB 57.7% 4310 11% DPnB 7% DPnB 19.2% Zerol 150 43% 4310 70%4310 22% Zerol 150 8% Zerol 150 4 28.6% PD — — one layer one layer 50.0%4310 16.7% Zerol 150

Example 25

In this example, PD=2 parts by wt PnB, 1 part DPnB.

Total Bottom Grams of PD Composition in Top Layer Layer Top Layer BottomLayer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0% 4310 2134 — — 25.0% 3GS 1 9.1% PD 21 41 7% PnB 5% PnB 68.2% 4310 4% DPnB 2%DPnB 22.7% 3GS 10% 4310 91% 4310 79% 3GS 2% 3GS 2 16.7% PD 21 48 16% PnB11% PnB 62.5% 4310 8% DPnB 5% DPnB 20.8% 3GS 18% 4310 81% 4310 58% 3GS3% 3GS 3 23.1% PD 20 57 17% PnB 15% PnB 57.7% 4310 9% DPnB 8% DPnB 19.2%3GS 18% 4310 71% 4310 56% 3GS 6% 3GS 4 28.6% PD 16 69 18% PnB 17% PnB50.0% 4310 9% DPnB 9% DPnB 16.7% 3GS 19% 4310 65% 4310 54% 3GS 9% 3GS 533.3% PD — — one layer one layer 50.0% 4310 16.7% 3GS

Example 26

In this example, PD=2 parts by wt PnB, 1 part DPnB.

Total Bottom Grams of PD Composition in Top Layer Layer Top Layer BottomLayer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0% 4310 2134 — — 25.0% HAB22 1 9.1% PD 23 39 7% PnB 5% PnB 68.2% 4310 4% DPnB 2%DPnB 22.7% HAB22 14% 4310 91% 4310 75% HAB22 2% HAB22 2 16.7% PD 25 4515% PnB 11% PnB 62.5% 4310 7% DPnB 5% DPnB 20.8% HAB22 28% 4310 78% 431050% HAB22 6% HAB22 3 23.1% PD — — One Layer One Layer 57.7% 4310 19.2%HAB22

Example 27

Grams of Total Bottom DMPD added Composition in Top Layer Layer TopLayer Bottom Layer to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0%4310 21 35 — — 25.0% Zerol 150 1 9.1% 1,5-DMPD 20 42 3% 1,5-DMPD 9%1,5-DMPD 68.2% 4310 13% 4310 89% 4310 22.7% Zerol 150 84% Zerol 150 2%Zerol 150 2 16.7% 1,5- 18 52 9% 1,5-DMPD 18% 1,5- DMPD 18% 4310 DMPD62.5% 4310 73% Zerol 150 77% 4310 20.8% Zerol 150 5% Zerol 150 3 23.1%1,5- 8 68 14% 1,5- 24% 1,5- DMPD DMPD DMPD 57.7% 4310 25% 4310 63% 431019.2% Zerol 150 61% Zerol 150 13% Zerol 150 4 28.6% 1,5- — — One LayerOne Layer DMPD 50.0% 4310 16.7% Zerol 150

Example 28

Total Bottom Grams of OP Composition in Top Layer Layer Top Layer BottomLayer added to Tube Tube Height, mm Height, mm wt % Wt % 0 75.0% 4310 2134 — — 25.0% Zerol 150 1 9.1% OP 22 40 7.8% OP 6.4% OP 68.2% 4310 16.3%4310 91.5% 4310 22.7% Zerol 150 75.9% Zerol 150 2.1% Zerol 150 2 16.7%OP 19 51 14.7% OP 13.4% OP 62.5% 4310 32.6% 4310 79.3% 4310 20.8% Zerol150 52.7% Zerol 150 7.3% Zerol 150 3 23.1% OP — — One Layer One Layer57.7% 4310 19.2% Zerol 150Results show compatibilizers of the present invention improve thesolubility between hydrofluorocarbons and conventional lubricants bydrawing significant amounts of refrigerant (4310) into the lubricantphase (top layer), and lubricant (3GS or Zerol 150) into the refrigerantphase (bottom layer). The compatibilizers improve solubilitysignificantly better than Isopar® H alone, which never reached onephase. The combination of PnB, DPnB and Isopar H surprisingly draws more4310 into the lubricant phase (17%) than either PnB, DPnB or Isopar Halone (15%, 13% and 0.4%) respectively after one gram is added. A mostpreferred compatibilizer by this method is 1-octyl pyrrolidin-2-one,which required only 3 grams to reach one layer with Zerol 150alkylbenzene lubricant.

Hexylene glycol was also tested as comparative data with HFC-4310mee andZerol 150 but the solution remained two layers even after 10 grams ofhexylene glycol was added.

Example 29

Lubricant return was tested in an lubricant-return apparatus as follows.Liquid refrigerant was fed from a pressurized cylinder through coppertubing to a heater where it was vaporized. The refrigerant vapor thenpassed through a pressure regulator and metering valve to control flowat a constant rate of 1,100 cc per minute and 101 kPa (1 atmosphere)pressure. The refrigerant vapor was fed to another copper tube 180 cm inlength and 0.635 cm outer diameter formed into a U-shape and placed in aconstant temperature bath. The U-shaped tube (U-tube) began with astraight vertical section 37 cm long then bent to a horizontal section27 cm long at the bottom of the bath. The tube then rose vertically in azigzag pattern with four 23 cm lengths, followed by another verticalstraight section 23 cm long. The U-tube was filled with 10 grams oflubricant, optionally containing compatibilizer, which was added to theU-tube through the 37 cm vertical tube. Vapor refrigerant passed slowlythrough the lubricant in the U-tube. Refrigerant and lubricant exitingthe U-tube was collected in a receiver and then the refrigerant allowedto evaporate from the lubricant. Lubricant was then weighed to determinehow much lubricant was carried out of the U-tube by the refrigerant.

Refrigerant R407C was placed in the refrigerant cylinder. Suniso 3GSmineral oil, or Suniso 3GS oil and compatibilizers of the presentinvention were placed in the copper U-tube, wherein the combinedlubricant and compatibilizer equaled 10 grams. The constant temperaturebath was held at a temperature of −20° C. Refrigerant R407C vapor wasfed through the U-tube at a flow rate of 1,100 cubic centimeters perminute and weight of lubricant in the receiver measured at 6, 10, and 20minute time intervals. Data are shown below.

Example 29

Lubricant Composition in Wt % Lubricant Returned U-tube 6 min 10 min 20min 6% 5-methyl-2-hexanone in 11.3 18.1 26.2 3GS 6% 2-Heptanone in 3GS12.7 20.0 28.1 Comparative Data POE 22 9.3 20.0 29.6 3GS 0 0 0 6%Isopar(R)H in 3GS 0 7.9 17.0

Results show the addition of 2-heptanone and 5-methyl-2-hexanone ketonecompatibilizers to 3GS mineral oil shows significant improvement inlubricant return versus neat 3GS or Isopar H in 3GS.

Example 30

The apparatus and procedure of Example 29 was used to test refrigerantHFC-134a with Zerol 150 alkylbenzene lubricant, with and withoutcompatibilizers. Results are shown below:

Example 30

Lubricant Composition in Wt % Lubricant Returned U-tube 6 Min 10 Min 20Min 10% PnB/5% DPnB in Zerol 15 24 34 150 10% PnB/5% DPnB/2% Syn- 17 2536 0-Ad 8478*** in Zerol 150 10% PnB/5% DPnB/0.5% 16 25 36 BHT in Zerol150 10% PnB/5%DPnB/1.5% n- 23 29 36 pentane in Zerol 150 10% PnB/5%DPnB/1.5% n- 21 30 39 octane in Zerol 150 10% PnB/5% DPnB/15% 15 27 38PVE 32 in Zerol 150 Comparative Data POE 22 16 27 36 Zerol 150  0  0  315% Ucon LB-65* in Zerol  0  4 19 150 15% Ucon 50-HB-100** in  0  0  7Zerol 150 *Ucon LB-65 is a polyoxyproplyene glycol lubricant sold byUnion Carbide with an average molecular weight of about 340. **Ucon50-HB-100 is a lubricant containing equal amounts of oxyethylene andoxpropylene groups sold by Union Carbide with an average molecularweight of about 520 ***Syn-0-Ad 8478 is an alkylated triaryl phosphateester produced by Akzo Chemicals

Results show addition of polyoxyalkylene glycol ether compatibilizers,optionally with additional additives such as antiwear agents orhydrocarbons, significantly improve lubricant return of alkylbenzenelubricant and provide performance equivalent to POE 22 polyol esterlubricant. The comparative data shows higher molecular weightpolyoxypropylene lubricants do not provide acceptable lubricant return.

Example 31

The apparatus and procedure of Example 29 was used to test refrigerantR404A with Zerol 150 alkyl benzene lubricant, with and withoutcompatibilizers versus POE22 polyol ester lubricant. Results are shownbelow.

Example 31

Wt % Wt % Wt % Lubricant Lubricant Lubricant Lubricant CompositionReturned Returned Returned in U-tube 6 Min 10 Min 20 Min 35% 1-octylpyrrolidin-2-one 26 36 45 in Zerol 150 12% DMM in Zerol 150 18 26 35 6%DMM/12% 1-octyl pyrro- 13 23 34 lidin-2-one/2% Synergol in Zerol 150 20%1,1-dibutyl formamide in 10 18 29 Zerol 150 20% 1-methyl caprolactam in12 24 36 Zerol 150 17% 1,3-dimethyoxybenzene 17 24 35 in Zerol 150Comparative Data POE 22  0  5 17 Zerol 150  0  0 <1

Results show addition of compatibilizers of the present invention toZerol 150 provide significantly improved lubricant return versus polyolester lubricant POE 22 polyol ester lubricant.

Example 32

The apparatus and procedure of Example 29 was used to test refrigerantHFC-134a with Zerol 150 alkyl benzene lubricant, with and withoutcompatibilizers versus POE 22 polyol ester lubricant. Results are shownbelow.

Example 32

Wt % Wt % Wt % Lubricant Lubricant Lubricant Lubricant CompositionReturned Returned Returned in U-tube 6 Min 10 Min 20 Min 15%Cycloheptanone/1% Orange* 27 35 42 in Zerol 150 15% 2-Nonanone/1%Orange* in 33 40 46 Zerol 150 15% Diisobutyl ketone/1% 31 37 43Cinnamon* in Zerol 150 20% DMPD in Zerol 150 32 38 44 20% Propyleneglycol tert- 25 32 38 butyl ether in Zerol 150 15% cyanoheptane in Zerol150 32 39 47 Comparative Data POE 22 19 29 37 Zerol 150  0  0  7*“Orange” and “Cinnamon” are fragrances sold by IntercontinentalFragrance

Results show addition of compatibilizers of the present invention toZerol 150 provide lubricant return comparable to POE 22 polyol esterlubricant.

Example 33

The apparatus and procedure of Example 29 was used to test refrigerantR401A with Suniso 3GS mineral oil lubricant, with and withoutcompatibilizers versus neat Zerol 150. Results are shown below.

Example 33

Wt % Wt % Wt % Lubricant Lubricant Lubricant Lubricant CompositionReturned Returned Returned in U-tube 6 Min 10 Min 20 Min 10%Chlorooctane in 3GS 25 36 46 15% Chlorooctane in 3GS 35 43 50Comparative Data Zerol 150  0 12 38 3GS  0  0  5

Results show the addition of compatibilizers of the present invention toSuniso 3GS provide improved lubricant return versus Zerol 150.

Example 34

The apparatus and procedure of Example 29 was used to test refrigerantR410A with Zerol 150 alkyl benzene lubricant, with and withoutcompatibilizers versus POE 22 polyol ester lubricant. Results are shownbelow.

Example 34

Wt % Wt % Wt % Lubricant Lubricant Lubricant Lubricant CompositionReturned Returned Returned in U-tube 6 Min 10 Min 20 Min 15% PnB inZerol 150 15  26  33  15% DPnB in Zerol 150 9 17  26  15% TPnB in Zerol150 0 10  19  15% PnP in Zerol 150 15  22  32  5% PnB/5% DPnB/5% 12  19 29  Isopar H in Zerol 150 5% PnB/5% DPnB/5% 15  23  33  Aromatic 150 inZerol 150 Comparative Data POE 22 0 11  22  Zerol 150 0 0 1 15%Propylene Glycol in Zerol 150 * * * 15% Dipropylene glycol in Zerol150 * * * 15% Ucon 50-HB100** in Zerol 150 0 0 6 *Not soluble in Zerol ®150 **Polyalkylene glycol lubricant sold by Union Carbide withoxyethylene and oxypropylene groups with an average molecular weight of520

Results show use of compatibilizers of the present invention in Zerol150 provide comparable to improved lubricant return versus POE 22 polyolester lubricant.

Example 35-36

Tests were conducted to determine if refrigerant R410A could be used inan HCFC-22 Carrier heat pump (Model Tech 2000), using Zerol 150alkylbenzene lubricant and compatibilizers of the present invention. Theheat pump was outfitted with an R410A Copeland scroll compressor(ZP32K3E R-410) equipped with a sight glass and level tube in thelubricant sump. The fan-coil unit was installed in the indoor room of anenvironmental chamber and the outdoor unit was installed in the outdoorroom. The two units were connected by 1.59 cm (⅝-inch) outer diametercopper tubing in the suction line and by 1.27 cm (½-inch) outer diametercopper tubing in the liquid line. The system was charged with 3,180grams of refrigerant and 1,110 grams of lubricant containingcompatibilizer. Refrigerant R410A with polyol ester lubricant was usedas a baseline for comparison. Tests were conducted at ASHRAE cooling andlow temperature heating conditions. For cooling the indoor room wascontrolled at 26.7° C. (80° F.) and 50% relative humidity, the outdoorroom at 27.8° C. (82° F.) and 40% relative humidity. For low temperatureheating, the indoor room was controlled at 21.1° C. (70° F.) and 57%relative humidity, the outdoor room at −8.3° C. (17° F.) and 60%relative humidity. Results from refrigerant side measurements are shownbelow.

Example 35 Cooling Test

Vol % Lubricant Capacity Lost From kB.t.u./hr Lubricant Composition Sump(cm) (kW) EER 15% PnB in Zerol 150 15% 2.91 (0.852) 11.29 20% PnB inZerol 200TD 14% 2.90 (0.849) 11.30 20% DPnB in Zerol 150 20% 2.90(0.849) 11.28 10% PnB/5% DPnB in 18% 2.93 (0.858) 11.61 Zerol 150 10%PnB/5% DPnB in HAB22 18% 3.00 (0.878) 11.50 10% PnB/5% DPnB in 3GS 26%2.92 (0.855) 11.08 18% PnB/10% DPnB in 4GS 23% 2.88 (0.843) 11.03 10%PnB/5% DPnB/15% 26% 2.92 (0.855) 11.14 HAB22 in 3GS 5% PnB/5% DPnB/5%Isopar 18% 2.94 (0.861) 11.48 H in Zerol 150 3% PnB/8% DPnB/4% 23% 2.95(0.864) 11.25 Aromatic 150 in Zerol 150 4% PnB/7% DPnB/4% DMM 20% 2.97(0.870) 11.32 in Zerol 150 10% PnB/5% DPnB/1.5% 20% 3.10 (0.908) 11.70Pentane in Zerol 150 10% PnB/5% DPnB/15% PVE 22% 3.00 (0.878) 11.67 32in Zerol 150 10% PnB/5% DPnB/15% PVE 20% 2.95 (0.864) 11.40 32 in 3GS 7%PnB/7% DPnB/7% TPnB 26% 2.92 (0.855) 11.18 in 3GS 15% BnB in 3GS 33%2.91 (0.852) 11.17 20% PTB in 3GS 27% 2.92 (0.855) 11.28 10% PnB/5%DPnB/2.5% 15% 2.96 (0.867) 11.41 BTPP in Zerol 150 Comparative Data POE22 10% 2.98 (0.873) 11.70 POE 32 12% 2.97 (0.870) 11.48 Zerol 150 30%2.86 (0.838) 10.97 Suniso 3GS 40% 2.86 (0.838) 10.82

Example 36 Low Temperature Heating Tests

Sump Lubricant Capacity Lubricant Composition Level (cm) kB.t.u/hr (kW)EER 10% PnB/5% DPnB in 4.6 20.2 (5.92) 8.38 Zerol 150 3% PnB/8% DPnB/4%4.4 20.4 (5.97) 8.45 Aromatic 150 in Zerol 150 10% PnB/5% DPnB in 4.920.4 (5.97) 8.42 HAB22 10% PnB/5% DPnB/2% 5.7 20.1 (5.89) 8.37 BTPP inZerol 150 15% PVE32/10% 4.6 19.9 (5.83) 8.30 PnB/5% DPnB in 3GS 5%PnB/5% DPnB/5% 4.7 20.2 (5.92) 8.35 Isopar H in Zerol 150 ComparativeData POE 22 5.5 20.0 (5.86) 8.35 Zerol 150 4.3 19.3 (5.65) 8.00

Results show significant increases in lubricant return, energyefficiency and capacity when compatibilizers are added to Zerol 150,Suniso 3GS or 4GS and several cases with performance equivalent to orsuperior than polyol esters. There is also significant EER improvementduring heating.

Example 37

The apparatus and procedure of Example 32 was used to test R410Arefrigerant with compatibilizers of the present invention. Results forcooling are in the table below.

Example 37

Sump Capacity Lubricant kB.t.u./hr Lubricant Composition Level (cm) (kW)EER 10% PnB/5% DPnB in 5.00 3.01 (0.882) 11.71 Zerol 150 10% PnB/5%DPnB/1.5% 4.95 3.04 (0.890) 11.98 Pentane in Zerol 150 Comparative DataPOE 22 5.72 3.09 (0.905) 12.04 1.5% Pentane in Zerol 150 4.40 2.93(0.858) 11.23

The data show that using only pentane provides inadequate lubricantreturn, capacity and energy efficiency. PnB/DPnB as compatibilizerprovides increased performance and a combination PnB/DPnB/pentane ascompatibilizer provides the best overall performance, includingcomparable EER with polyol ester lubricant POE22.

Example 38

The apparatus and procedure of Example 32 was used to test R410Arefrigerant with compatibilizers of the present invention. In this test,however, the HCFC-22 evaporator was replaced with and R410A evaporator.Results for cooling are below.

Example 38

Sump Capacity Lubricant kB.t.u./hr Lubricant Composition Level (cm) (kW)EER 10% 2-heptanone/1% orange* 5.33 3.17 (0.928) 11.87 in Zerol 150 15%2-nonanone/1% cinnamon* 5.60 3.15 (0.923) 11.89 in Zerol 150 20% DMPD inZerol 150 5.70 3.15 (0.923) 11.92 10% PnB/10% DMPD in 5.50 3.16 (0.925)11.94 Zerol 150 20% 1,5-DMPD in Zerol 150 5.90 3.14 (0.920) 11.97Comparative Data POE 22 6.80 3.35 (0.981) 12.55 Zerol 150 4.27 3.07(0.899) 11.30 *“Orange” and “Cinnamon” are fragrances sold byIntercontinental Fragrance

The data shows a significant improvement in capacity, energy efficiencyand lubricant return using compatibilizers versus neat Zerol 150, eventhough the system had an HCFC-22 condenser and an R410A evaporator.

Example 39

Tests were conducted to determine if R410A refrigerant could be used inan R410A heat pump using Zerol 150 alkylbenzene lubricant andcompatibilizers. The heat pump was outfitted a sight glass and leveltube in the lubricant sump. The fan-coil unit was installed in theindoor room of an environmental chamber and the outdoor unit wasinstalled in the outdoor room. The two units were connected by 1.59 cm(⅝-inch) outer diameter copper tubing in the suction line and by 1.27 cm(½-inch) outer diameter copper tubing in the liquid line. The system wascharged with 3,860 grams of refrigerant and 1270 ml of lubricantcontaining compatibilizers of the present invention. Refrigerant R410Awith POE 22 polyol ester lubricant was used as a baseline forcomparison. Tests were conducted at ASHRAE cooling conditions. Forcooling the indoor room was controlled at 26.7° C. (80° F.) and 50%relative humidity, the outdoor room at 27.8° C. (82° F.) and 40%relative humidity. Results from refrigerant side measurements are shownbelow.

Example 39 Cooling Test

Vol % Lubricant Capacity Lost From kB.t.u./hr Lubricant Composition Sump(cm) (kW) EER 10% PnB/5% DPnB in Zerol 16% 3.04 (0.890) 12.59 150 10%PnB/5% DPnB/in Zerol 17% 3.05 (0.893) 12.67 150 with R410A + 0.5%pentane 10% PnB/5% DPnB in Zerol 23% 3.03 (0.887) 13.06 150 with R410A +0.5% 1,1,1,3,3-pentafluoropropane 10% PnB/5% DPnB in Zerol 19% 3.04()    13.11 150 with R410A + 0.5% 1,1- dichloro-1,1,1-trifluoroethane12% DMM in Zerol 150 20% 3.04 (0.890) 12.88 11% Diisobutyl ketone/1% 21%3.02 (0.884) 12.99 orange** in Zerol 150 11% 2-Nonanone/1% 20% 3.03(0.887) 13.02 cinnamon** in Zerol 150 20% 1-octyl-pyrrolidin-2-one 18%3.07 (0.899) 13.35 in Zerol 150 45% 1-octyl-pyrrolidin-2-one 13% 3.09(0.905) 13.50 in Zerol 150 20% N-methylcaprolactam in 21% 3.11 (0.911)13.56 Zerol 150 Comparative Data POE 22 10% 3.09 (0.905) 13.54 Zerol150* 38% 2.96 (0.867) 12.43 *Zerol 150 test was stopped beforecompletion - compressor sump lubricant level became too low **“Orange”and “Cinnamon” are fragrances sold by Intercontinental FragranceResults show improved lubricant return, capacity and efficiency whencompatibilizers of the present invention are added to Zerol 150. Use of1-octyl pyrrolidin-2-one amide compatibilizer shows performanceequivalent to the POE 22 polyol ester lubricant baseline.

Example 40

Tests were conducted to determine if HFC-134a refrigerant could be usedin a domestic refrigerator (Whirlpool 21 cubic foot) using conventionallubricants Zerol 150 or Suniso 3GS and compatibilizers of the presentinvention. The refrigerator was outfitted with pressure and temperaturemeasuring devices as well as power measurement to the hermeticreciprocating compressor and two fans. The compressor was also fittedwith a sight glass to monitor lubricant level during operation. Therefrigerator was tested in a room controlled at 27.8° C. and 40%relative humidity. The refrigerator was turned on and allowed to cooluntil the refrigerated compartment reached 3.3° C. The energy efficiency(COP) and capacity were then calculated using a thermodynamic modelbased on temperature, pressure and power inputs. In all tests, lubricantlevel was adequate indicating no lubricant return problems.

Example 40

Lubricant Capacity % Change in % Change in Composition (Watts) Capacityvs POE COP COP vs POE 10% PnB/5% DPnB 145 +1.4% 1.31 +8.3% in Zerol 15012% DMM in 3GS 143 — 1.33 +9.9% 12% DMM in Zerol 145 +1.4% 1.34 +10.7%150 6% DMM in Zerol 148 +3.5% 1.30 +7.4% 100 20% OP in Zerol 145 +1.4%1.30 +7.4% 100 45% OP in Zerol 146 +2.1% 1.32 +9.1% 300 Comparative DataPOE 22 143 — 1.21 — Zerol 150 * * * * Zerol 75 146 +2.1% 1.25 +3.3% *Evaporator was flooded and test could not be completed.Results show a significant improvement in energy efficiency whencompatibilizers of the present invention are used with conventionallubricants. Improvement is also shown when compared with using a lowviscosity alkyl benzene lubricant (Zerol 75) alone. Capacities alsoshowed improvement versus POE 22 polyol ester lubricant.

Example 41

Compatibilizers of the present invention were mixed with Zerol 150 andplaced in shallow dishes in a 50% constant humidity chamber. Periodicsamples of the compositions were taken and analyzed by Karl Fischertitration for water. Results are shown in ppm water versus polyol ester,polyvinyl ether and polyalkylene glycol lubricants.

Example 41

Samples Hours 0 2 3.5 5.5 21 26 45 50 69 74 15% DIP in Zerol 150 77 108124 154 318 351 402 392 401 375 10% PnB 5% DPnB in 112 137 209 242 506533 538 661 756 708 Zerol 150 Comparative Data PVE32 185 398 505 7851784 1917 2511 2451 2791 2630 Zerol 150 43 47 36 41 37 33 30 29 39 34Ucon488 1175 1517 3123 4158 12114 12721 16741 18592 20133 19997 POE 22153 165 173 181 693 733 1022 1096 1199 1165

Results show compatibilizer/lubricant compositions of the presentinvention absorb less water than polyol ester and significantly lesswater than polyvinyl ether and polyalkylene glycol lubricants. Sincecompatibilizer/lubricant compositions of the present invention do absorbsome water, they also have lower risk of having free (immisicible) wateravailable than Zerol 150. Free water can freeze in expansion devices andcause compressor failure.

Example 42

Compositions of the present invention were tested for thermal stability.Stainless steel, aluminum and copper coupons were placed in sealed glasstubes containing R410A refrigerant, Zerol 150 lubricant andcompatibilizers of the present invention. In four cases, 1,000 ppm waterwas added. Tubes were held for 14 days at 175° C. Results are shown inthe table below.

Example 42

R410A/Zerol 150 + R407C/Zerol R410A/Zerol Comparative 5% DMM/5% 100 +20% 1- 150 + 10% Data: After 14 DPnB/5% 140 octylpyrrolidin- PnB/5%DPnB + R410A/POE days at R410A/Zerol Naptha + 1000 2-one + 1000 1000 ppm22 + 1000 ppm 175° C. 150 + 15% PnB ppm H₂O ppm H₂O H₂O H2O Copper Noobservable No observable No observable No observable Corrosion andAppearance changes changes changes changes discoloration observedAluminum No observable No observable No observable No observable Noobservable Appearance changes changes changes changes changes Steel Noobservable No observable No observable No observable No observableAppearance changes changes changes changes changes Acidity as <1 <1 <129   577 HCl in ppm R410A 99.9 99.9 99.9 99.9  99.8 wt %

Results show compositions of the present invention are thermally stableeven in the presence of 1,000 ppm water, indicating no acid formation.Polyol ester lubricant in the presence of water caused corrosion ofcopper due to hydrolysis and acid formation.

Example 43

Volume resistivity was measured by ASTM D-1169 method using a Balsbaughliquid test cell connected to a Keithley model 617 electrometer. AKeithley model 247 high voltage power supply was used as the excitationsource. Capacitance used for calculating both resistivity and dielectricconstant was measured with a GenRad model 1189 capacitance bridge.Results are shown below.

Example 43

Volume Resistivity Composition (Ohm × cm) Dielectric Constant Zerol150/PnB/DPnB 9.12 × 10¹² 2.73 (85/10/5 wt %) Zerol 150/PnB/DPnB/Isopar1.73 × 10¹³ 2.62 H (85/5/5/5 wt %) Comparative Data POE 22 5.50 × 10¹¹3.54Results show compositions of the present invention have improvedelectrical properties versus POE 22 polyol ester lubricant. They show anincrease in volume resistivity and a decrease in dielectric constantthat improves electrical insulating properties and protects compressorelectrical motor winding materials.

Example 44

Solubility and viscosity measurements were made for compositions of thepresent invention in Zerol 150 with R410A refrigerant. The data wereused to determine the amount of refrigerant dissolved in lubricant underevaporator conditions at 10° C., 1 MPa and subsequent viscosityreduction. Data were compared with R410A/POE 22 and R410A/Zerol 150. Theviscosity and percent refrigerant dissolved in lubricant at compressionconditions was also determined, 80° C., 2.5 MPa. Results are shownbelow.

Example 44

% Refrigerant % Refrigerant Dissolved in Viscosity Dissolved inViscosity Lubricant at (cPoise) at Lubricant at (cPoise) at EvaporatorEvaporator at Compression Compressor at Composition Conditions 10° C.Conditions 80° C. R410A/10% PnB + 18 8 11 2.5 5% DPnB in Zerol 150Comparative Data R410A/POE22 45 3 17 3.1 R410A/Zerol 150 10 38   7 3.2

Results show a significant increase in refrigerant solubility andsubsequent viscosity reduction in the evaporator by a compatibilizer ofthe present invention when added to a conventional alkyl benzenelubricant. This viscosity reduction can result in improved lubricantreturn to the compressor. Because less refrigerant is dissolved in thelubricant than POE 22 at compression conditions, viscosity remains highenough to effectively lubricate the compressor.

Example 45

Dynamic viscosity measurements were made using a ViscoPro2000 viscometerof POE 22, Zerol 150 and Zerol 150 containing 10 wt % PnB and 5 wt %DPnB. Results are shown in FIG. 10. Results show 10% PnB and 5% DPnBincrease the viscosity index of Zerol 150. This gives the desirableresult of lower viscosity at low temperature without lowering viscosityat high temperature, a profile similar to POE 22. This enhanceslubricant return from the evaporator while maintaining good viscosity inthe compressor.

Example 46

A four ball wear test using ASTM D4172B was conducted using steel ballswas conducted to assess the lubricating properties for compositions ofthe present invention. The test was run for 60 minutes using differentcombinations of compatibilizer in alkyl benzene lubricant and comparedto lubricant without compatibilizer. Wear scar and average coefficientof friction were measured. Results are shown below.

Average Coefficient Wear Scar (mm) of Friction 6% DMM in Zerol 100 0.850.108 20% 1-octyl pyrrolidin-2-one 0.61 0.093 in Zerol 100 35% 1-octylpyrrolidin-2-one 0.64 0.091 in Zerol 150 12% DMM/2% 0.52 0.113 Synergolin Zerol 150 Comparative Data Zerol 150 0.88 0.110Results show lubrication properties are similar or improved whencompatibilizers of the present invention are added to conventionallubricants, as evidenced by reduced size of wear scar and similar lowercoefficient of friction. Addition of antiwear additives such as Synergolfurther improves lubrication properties.

Example 47

Compressor durability tests were conducted with compositions of thepresent invention. A flooded start test was performed on scroll androtary compressors. A flooded start test is a severe condition where thecompressor sump is flooded with refrigerant on shutdown. During startup,presence of refrigerant can reduce lubricant viscosity resulting ininadequate compressor lubrication. This is particularly difficult withimmiscible refrigerant/lubricant systems where two layers can form inthe compressor sump with the refrigerant layer on the bottom, the pointat which lubricant is normally drawn into the compressor bearings. Thecompressors were tested at −12.2° C. suction temperature and 37.8° C.discharge temperature. The compressors were cycled for three minutes onand fifteen mutes off for 1,000 cycles. After the tests the compressorswere disassembled and inspected for wear. No significant wear wasobserved.

Example 47

Compressor Type Refrigerant Lubricant Significant Wear Rotary R407C 10%PnB/5% DPnB None in Zerol 150 Scroll R407C 10% PnB/5% DPnB None in Zerol150 Comparative Data Rotary HCFC-22 Mineral Oil None Scroll HCFC-22Mineral Oil None

Example 48

Compatibilizers of the present invention were tested for compatibilitywith polyester motor materials used in certain hermetic compressors.Strips of polyester film were placed in a sealed tube with HFC-134arefrigerant and different lubricant/compatibilizer combinations. Thetubes were held at 150° C. for two weeks. The polyester strips wereremoved and bent ten times through an arc of 180° to evaluate forembrittlement. Strips in both the liquid and vapor phases wereevaluated. Results are shown in the table below.

Example 48

Lubricant tested # of Bends Before # of Bends Before with HFC-134aBreaking Liquid Phase Breaking Vapor Phase 10% PnB/5% DPnB 1 1 in Zerol150 12% DMM in Zerol 150 >10 >10 20% 1-octyl >10 >10 pyrrolidin-2-one inZerol 150 Comparative Data Zerol 150 7 9 POE 22 10  1The data show DMM (CH₃O[CH₂CH(CH₃)O]₂CH₃) with no free hydroxyl groupshas significantly improved polyester motor material compatibility versusPnB (C₄H₉OCH₂CH(CH₃)OH) and DPnB (C₄H₉O(CH₂CH(CH₃)O)₂H), both withterminal hydroxyl groups. The data also show alkyl pyrrolidones such as1-octyl-2-pyrrolidone are compatible with polyester motor materials andpreferred for use in certain hermetic compressors.

1. A lubricant composition for use in compression refrigeration and airconditioning, comprising: (a) at least one lubricant selected from thegroup consisting of paraffins, napthenes, aromatics and poly-α-olefins;(b) at least one compatibilizer selected from the group consisting of:amides represented by the formulae wherein cyclo-[(CR⁶R⁷)_(n)CON(R⁵)—],wherein n is selected from integers from 3 to 5, R⁶ and R⁷ are hydrogenor contain a single saturated hydrocarbon radical among the n methyleneunits, and R⁵ is selected from saturated hydrocarbon radicals containingfrom 1 to 12 carbon atoms, and where said amides have a molecular weightof from about 160 to about 250 atomic mass units and a carbon to oxygenratio of from about 7 to about
 16. 2. A refrigerant composition for usein compression refrigeration and air conditioning, comprising: (a) atleast one halogenated hydrocarbon selected from the group consisting ofhydrofluorocarbons and hydrofluorochlorocarbons; (b) at least onelubricant selected from the group consisting of paraffins, naphthenesaromatics and poly-α-olefins; and (c) at least one compatibilizerselected from amides represented by the formulacyclo-[(CR⁶R⁷)_(n)CON(R⁵)—], wherein n is selected from integers from 3to 5, R⁶ and R⁷ are hydrogen or contain a single saturated hydrocarbonradical among the n methylene units, and R⁵ is selected from saturatedhydrocarbon radicals containing from 1 to 12 carbon atoms, and wheresaid amides have a molecular weight of from about 160 to about 250atomic mass units and a carbon to oxygen ratio of from about 7 to about16.
 3. A refrigerant composition for use in compression refrigerationand air conditioning apparatus containing paraffinic, napthenic,aromatic and/or poly-α-olefinic lubricant, said refrigerant compositioncomprising: (a) at least one halogenated hydrocarbon selected from thegroup consisting of hydrofluorocarbons and hydrochlorofluorocarbons; and(b) at least one compatibilizer selected from amides represented by theformula cyclo-[(CR⁶R⁷)_(n)CON(R⁵)—], wherein n is selected from integersfrom 3 to 5, R⁶ and R⁷ are hydrogen or contain a single saturatedhydrocarbon radical among the n methylene units, and R⁵ is selected fromsaturated hydrocarbon radicals containing from 1 to 12 carbon atoms, andwhere said amides have a molecular weight of from about 160 to about 250atomic mass units and a carbon to oxygen ratio of from about 7 to about16.
 4. A process for returning lubricant from a non-compressor zone to acompressor zone in a compression refrigeration system comprising: (a)contacting lubricant selected from the group consisting of paraffins,naphthenes, aromatics, and polyalphaolefins, in said non-compressor zonewith a halogenated hydrocarbon selected from the group consisting ofhydrofluorocarbons and hydrochlorofluorocarbons, in the presence of acompatibilizer to form a solution comprising said lubricant, saidhalogenated hydrocarbon, and said compatibilizer; and (b) transferringsaid solution from said non-compressor zone to said compressor zone ofsaid refrigeration system; wherein said compatibilizer is selectedamides represented by the formula cyclo-[(CR⁶R⁷)_(n)CON(R⁵)—], wherein nis selected from integers from 3 to 5, R⁶ and R⁷ are hydrogen or containa single saturated hydrocarbon radical among the n methylene units, andR⁵ is selected from saturated hydrocarbon radicals containing from 1 to12 carbon atoms, and where said amides have a molecular weight of fromabout 160 to about 250 atomic mass units and a carbon to oxygen ratio offrom about 7 to about
 16. 5. A method of solubilizing a halogenatedhydrocarbon refrigerant, said halogenated hydrocarbon refrigerantselected from the group consisting of hydrofluorocarbons andhydrochlorofluorocarbons, in a lubricant said lubricant selected fromthe group consisting of paraffins, naphthenes, aromatics, andpolyalphaolefins, which comprises the steps of contacting said lubricantwith said halogenated hydrocarbon refrigerant in the presence of aneffective amount of a compatibilizer and forming a solution of saidlubricant and said halogenated hydrocarbon refrigerant, wherein saidcompatibilizer is selected from the group consisting of: amidesrepresented by the formula cyclo-[(CR⁶R⁷)_(n)CON(R⁵)—], wherein n isselected from integers from 3 to 5, R⁶ and R⁷ are hydrogen or contain asingle saturated hydrocarbon radical among the n methylene units, and R⁵is selected from saturated hydrocarbon radicals containing from 1 to 12carbon atoms, and where said amides have a molecular weight of fromabout 160 to about 250 atomic mass units and a carbon to oxygen ratio offrom about 7 to about
 16. 6. A method of lubricating a compressor in acompression refrigeration apparatus containing a halogenated hydrocarbonrefrigerant selected from the group consisting of hydrofluorocarbons andhydrochlorofluorocarbons, comprising the step of adding to saidcompressor a composition comprising: (a) at least one lubricant selectedfrom the group consisting of paraffins, naphthenes, aromatics, andpolyalphaolefins; and (b) at least on compatibilizer selected from thegroup consisting of: amides represented by the formulacyclo-[(CR⁶R⁷)_(n)CON(R⁵)—], wherein n is selected from integers from 3to 5, R⁶ and R⁷ are hydrogen or contain a single saturated hydrocarbonradical among the n methylene units, and R⁵ is selected from saturatedhydrocarbon radicals containing from 1 to 12 carbon atoms, and wheresaid amides have a molecular weight of from about 160 to about 250atomic mass units and a carbon to oxygen ratio of from about 7 to about16.